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V. LIST OF ABBREVIATIONS

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TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

V. <strong>LIST</strong> <strong>OF</strong> <strong>ABBREVIATIONS</strong><br />

Abbreviation Chemical Name Chemical Structure<br />

O<br />

18-Cr-6<br />

18-crown-6<br />

O<br />

O<br />

O<br />

O<br />

O<br />

Ac<br />

acetyl<br />

O<br />

acac<br />

acetylacetonyl<br />

O<br />

O<br />

AA asymmetric aminohydroxylation NA<br />

AD asymmetric dihydroxylation NA<br />

ad<br />

adamantyl<br />

ADDP 1,1'-(azodicarbonyl)dipiperidine N N<br />

N<br />

O<br />

O<br />

N<br />

ADMET acyclic diene metathesis polymerization NA<br />

O<br />

acaen<br />

N,N’-bis(1-methyl-3-oxobutylidene)ethylenediamine<br />

O<br />

N<br />

N<br />

AIBN 2,2'-azo bisisobutyronitrile N N<br />

N<br />

N<br />

Alloc<br />

allyloxycarbonyl<br />

O<br />

O<br />

Am<br />

amyl (n-pentyl)<br />

An p-anisyl O<br />

ANRORC anionic ring-opening ring-closing NA<br />

aq aqueous NA<br />

O<br />

AQN<br />

anthraquinone<br />

O<br />

Ar<br />

aryl (substituted aromatic ring)<br />

NA<br />

xvii


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

ATD<br />

aluminum tris(2,6-di-tert-butyl-4-methylphenoxide)<br />

Al<br />

O<br />

atm 1 atmosphere = 10 5 Pa (pressure) NA<br />

3<br />

Ph<br />

ATPH<br />

aluminum tris(2,6-diphenylphenoxide)<br />

Al<br />

O<br />

Ph<br />

3<br />

BBN (9-BBN)<br />

9-borabicyclo[3.3.1]nonane (9-BBN)<br />

H<br />

B<br />

B<br />

9-borabicyclo[3.3.1]nonyl<br />

B<br />

BCME bis(chloromethyl)ether Cl O<br />

Cl<br />

O<br />

BCN<br />

N-benzyloxycarbonyloxy-5-norbornene-2,3-<br />

dicarboximide<br />

O<br />

N<br />

O<br />

O<br />

O<br />

BDPP<br />

(2R, 4R) or (2S, 4S) bis(diphenylphosphino)pentane<br />

Ph 2 P PPh 2<br />

(R)<br />

(R)<br />

BER borohydride exchange resin NA<br />

OH<br />

BHT<br />

2,6-di-t-butyl-p-cresol (butylated hydroxytoluene)<br />

BICP<br />

2(R)-2’(R)-bis(dipenylphosphino)-1(R),1’(R)-<br />

dicyclopentane<br />

(R) (R)<br />

(R)<br />

(R)<br />

Ph 2 P PPh 2<br />

BINAL-H<br />

2,2'-dihydroxy-1,1'-binaphthyl lithium aluminum<br />

hydride<br />

O H<br />

O Al H<br />

Li<br />

BINAP 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl PPh 2<br />

PPh 2<br />

xviii


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

BINOL<br />

1,1'-bi-2,2'-naphthol<br />

OH<br />

OH<br />

Bip<br />

biphenyl-4-sulfonyl<br />

O<br />

S<br />

O<br />

bipy<br />

2,2'-bipyridyl<br />

N<br />

N<br />

BLA<br />

Brönsted acid assisted chiral Lewis acid<br />

NA<br />

bmin 1-butyl-3-methylimidazolium cation<br />

N N<br />

BMS<br />

Borane-dimethyl sulfide complex<br />

H 3<br />

B SMe 2<br />

Bn<br />

benzyl<br />

O<br />

BNAH 1-benzyl-1,4-dihydronicotinamide N<br />

NH 2<br />

BOB<br />

4-benzyloxybutyryl<br />

O<br />

O<br />

Boc<br />

t-butoxycarbonyl<br />

O<br />

O<br />

BOM<br />

benzyloxymethyl<br />

O<br />

BOP-Cl<br />

bis(2-oxo-3-oxazolidinyl)phosphinic chloride<br />

O<br />

O<br />

O Cl<br />

P<br />

N N<br />

O<br />

O<br />

bp boiling point NA<br />

BPD<br />

bis(pinacolato)diboron<br />

O<br />

O<br />

B<br />

B<br />

O<br />

O<br />

O<br />

BPO<br />

benzoyl peroxide<br />

O<br />

Ph<br />

O<br />

O<br />

Ph<br />

BPS (TBDPS) t-butyldiphenylsilyl<br />

Si<br />

xix


TABLE <strong>OF</strong> CONTENTS<br />

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Abbreviation Chemical Name Chemical Structure<br />

BQ benzoquinone O O<br />

Bs brosyl =<br />

(4-bromobenzenesulfonyl)<br />

O<br />

S<br />

O<br />

Br<br />

BSA<br />

N,O-bis(trimethylsilyl)acetamide<br />

Si<br />

N<br />

O<br />

Si<br />

BSA Bovine serum albumin NA<br />

Bt<br />

1- or 2-benzotriazolyl<br />

N<br />

N<br />

N<br />

BTAF benzyltrimethylammonium fluoride N<br />

F<br />

BTEA benzyltriethylammonium N<br />

BTEAC benzyltriethylammonium chloride N<br />

Cl<br />

BTFP<br />

3-bromo-1,1,1-trifluoro-propan-2-one<br />

O<br />

Br<br />

F<br />

F<br />

F<br />

BTMA benzyltrimethylammonium N<br />

BTMSA bis(trimethylsilyl) acetylene<br />

Si Si<br />

BTS<br />

bis(trimethylsilyl) sulfate<br />

O<br />

O<br />

Si S Si<br />

O<br />

O<br />

BTSA<br />

benzothiazole 2-sulfonic acid<br />

HO<br />

O<br />

S<br />

O<br />

S<br />

N<br />

BTSP<br />

bis(trimethylsilyl) peroxide<br />

O Si<br />

Si O<br />

Bz<br />

benzoyl<br />

O<br />

Bu ( n Bu)<br />

n-butyl<br />

c cyclo NA<br />

xx


TABLE <strong>OF</strong> CONTENTS<br />

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Abbreviation Chemical Name Chemical Structure<br />

ca<br />

circa<br />

NA<br />

(approximately)<br />

CA chloroacetyl<br />

O<br />

cerium(IV) ammonium nitrate (cericammonium<br />

CAN<br />

nitrate)<br />

cat. catalytic NA<br />

Cl<br />

Ce(NH 4 ) 2 (NO 3 ) 6<br />

CB<br />

catecholborane<br />

O<br />

HB<br />

O<br />

H<br />

Ph Ph<br />

CBS<br />

Corey-Bakshi-Shibata reagent<br />

N<br />

B<br />

O<br />

R<br />

R = H, alkyl<br />

Cbz (Z)<br />

benzyloxycarbonyl<br />

O<br />

O<br />

cc. or conc. concentrated NA<br />

CCE constant current electrolysis NA<br />

O<br />

CDI<br />

carbonyl diimidazole<br />

N<br />

N<br />

N<br />

N<br />

CHD<br />

1,3 or 1,4-cyclohexadiene<br />

1,3-CHD<br />

1,4-CHD<br />

CHIRAPHOS<br />

2,3-bis(diphenylphosphino)butane<br />

Ph<br />

P<br />

Ph<br />

(S)<br />

(S)<br />

Ph<br />

P<br />

Ph<br />

Chx (Cy)<br />

cyclohexyl<br />

Cl<br />

CIP<br />

2-chloro-1,3-dimethylimidazolidinium<br />

hexafluorophosphate<br />

CM (XMET) cross metathesis NA<br />

N<br />

NH<br />

PF 6<br />

CMMP cyanomethylenetrimethyl phosphorane P<br />

N<br />

COD<br />

1,5-cyclooctadiene<br />

COT<br />

1,3,5-cyclooctatriene<br />

Cp<br />

cyclopentadienyl<br />

O<br />

CPTS<br />

collidinium-p-toluenesulfonate<br />

S O<br />

O<br />

H<br />

N<br />

xxi


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Abbreviation Chemical Name Chemical Structure<br />

CRA<br />

Cr-PILC<br />

complex reducing agent<br />

chromium-pillared clay catalyst<br />

NA<br />

NA<br />

CSA<br />

camphorsufonic acid<br />

O<br />

SO 3 H<br />

CSI<br />

chlorosulfonyl isocyanate<br />

O<br />

N<br />

S C<br />

Cl<br />

O<br />

O<br />

CTAB<br />

cetyl trimethylammonium bromide<br />

N<br />

Br<br />

CTACl<br />

cetyl trimethylammonium chloride<br />

N<br />

Cl<br />

C 15 H 31<br />

CTAP<br />

cetyl trimethylammonium permanganate<br />

N MnO 4<br />

C 15 H 31<br />

Δ heat NA<br />

d days (length of reaction time) NA<br />

DABCO<br />

1,4-diazabicyclo[2.2.2]octane<br />

N<br />

N<br />

N<br />

N<br />

DAST diethylaminosulfur trifluoride F S N<br />

F<br />

F<br />

DATMP<br />

diethylaluminum 2,2,6,6-tetramethylpiperidide<br />

N<br />

AlEt 2<br />

DBA (dba)<br />

dibenzylideneacetone<br />

Ph<br />

Ph<br />

O<br />

O<br />

DBAD di-tert-butylazodicarboxylate N<br />

O N<br />

O<br />

O<br />

O<br />

DBI dibromoisocyanuric acid N<br />

Br<br />

N<br />

Br<br />

O<br />

NH<br />

O<br />

xxii


TABLE <strong>OF</strong> CONTENTS<br />

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Abbreviation Chemical Name Chemical Structure<br />

O<br />

O<br />

DBM<br />

dibenzoylmethane<br />

DBN<br />

1,5-diazabicyclo[4.3.0]non-5-ene<br />

8<br />

9<br />

7<br />

1 2 N<br />

3<br />

6 N<br />

4<br />

5<br />

DBS<br />

dibenzosuberyl<br />

DBU<br />

1,8-diazabicyclo[5.4.0]undec-7-ene<br />

10<br />

9<br />

11<br />

N<br />

8<br />

1 2 3<br />

N<br />

4<br />

7 5<br />

6<br />

CN<br />

DCA<br />

9,10-dicyanoanthracene<br />

CN<br />

Cl<br />

DCB 1,2-dichlorobenzene<br />

Cl<br />

DCC<br />

dicyclohexylcarbodiimide<br />

N C<br />

N<br />

DCE<br />

1,1-dichloroethane<br />

Cl<br />

Cl<br />

DCM dichloromethane CH 2 Cl 2<br />

CN<br />

DCN<br />

1,4-dicyanonaphthalene<br />

CN<br />

Dcpm<br />

dicyclopropylmethyl<br />

DCU<br />

N,N’-dicyclohexylurea<br />

O<br />

N<br />

H<br />

N<br />

H<br />

O<br />

DDQ<br />

2,3-dichloro-5,6-dicyano-1,4-benzoquinone<br />

NC<br />

NC<br />

O<br />

Cl<br />

Cl<br />

de<br />

diastereomeric excess<br />

NA<br />

xxiii


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Abbreviation Chemical Name Chemical Structure<br />

DEAD diethyl azodicarboxylate N N<br />

O<br />

O<br />

O<br />

O<br />

DEIPS diethylisopropylsilyl Si<br />

DEPBT<br />

3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-<br />

4(3H)-one<br />

EtO<br />

OEt<br />

O<br />

P<br />

O<br />

O<br />

N<br />

N<br />

N<br />

DET<br />

diethyl tartrate<br />

O<br />

O<br />

HO<br />

OH<br />

(R)<br />

(R)<br />

O<br />

O<br />

DHP<br />

3,4-dihydro-2H-pyran<br />

O<br />

OMe<br />

DHQ<br />

dihydroquinine<br />

H<br />

OH<br />

N<br />

N<br />

H<br />

(DHQ) 2 PHAL<br />

bis(dihydroquinino)phthalazine<br />

MeO<br />

Et<br />

H<br />

N<br />

H<br />

O<br />

N<br />

N<br />

H<br />

O<br />

N<br />

H<br />

Et<br />

OMe<br />

N<br />

N<br />

OMe<br />

DHQD<br />

dihydroquinidine<br />

H<br />

N<br />

N<br />

H OH<br />

(DHQD) 2 PHAL<br />

bis(dihydroquinidino)phthalazine<br />

MeO<br />

H<br />

N<br />

H<br />

O<br />

Et<br />

N<br />

Et<br />

N<br />

H<br />

O<br />

N<br />

H<br />

OMe<br />

N<br />

N<br />

O<br />

N<br />

DIAD diisopropyl azodicarboxylate<br />

O N<br />

O<br />

O<br />

O<br />

DIB<br />

(BAIB or PIDA)<br />

(diacetoxyiodo)benzene<br />

O<br />

I<br />

O<br />

O<br />

xxiv


TABLE <strong>OF</strong> CONTENTS<br />

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Abbreviation Chemical Name Chemical Structure<br />

DIBAL (DIBAH)<br />

DIBAL-H<br />

diisobutylaluminum hydride<br />

H<br />

Al<br />

DIC<br />

diisopropyl carbodiimide<br />

N<br />

C<br />

N<br />

O<br />

(R)<br />

PPh 2<br />

diop<br />

4,5-bis-[(diphenylphosphanyl)methyl]-2,2-dimethyl-<br />

[1,3]dioxolane<br />

O (R)<br />

PPh 2<br />

O<br />

DIPAMP 1,2-bis(o-anisylphenylphosphino)ethane P<br />

P<br />

O<br />

DIPEA<br />

(Hünig's base)<br />

diisopropylethylamine<br />

N<br />

DIPT<br />

diisopropyl tartrate<br />

O<br />

O<br />

HO<br />

OH<br />

(R) (R)<br />

O<br />

O<br />

O<br />

DLP<br />

dilauroyl peroxide<br />

C 10 H 21<br />

O<br />

O C 10 H 21<br />

O<br />

O<br />

DMA (DMAC)<br />

N,N-dimethylacetamide<br />

N<br />

DMAD<br />

dimethyl acetylene dicarboxylate<br />

O<br />

O<br />

O<br />

O<br />

DMAP N,N-4-dimethylaminopyridine N N<br />

DMB<br />

m-dimethoxybenzene<br />

O<br />

O<br />

DMDO dimethyl dioxirane O<br />

O<br />

O<br />

DME 1,2-dimethoxyethane O<br />

xxv


TABLE <strong>OF</strong> CONTENTS<br />

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Abbreviation Chemical Name Chemical Structure<br />

DMF<br />

N,N-dimethylformamide<br />

O<br />

H<br />

N<br />

O<br />

DMI 1,3-dimethylimidazolidin-2-one N N<br />

O<br />

DMP<br />

Dess-Martin periodinane<br />

AcO<br />

O<br />

I<br />

OAc<br />

OAc<br />

DMPS<br />

dimethylphenylsilyl<br />

Si<br />

DMPU<br />

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone<br />

(N,N-dimethyl propylene urea)<br />

N<br />

N<br />

O<br />

DMTSF dimethyl(methylthio)sulfonium tetrafluoroborate Me S S Me<br />

Me<br />

BF 4<br />

DMS dimethylsulfide S<br />

DMSO<br />

dimethylsulfoxide<br />

O<br />

S<br />

DMT<br />

4,4’-dimethoxytrityl<br />

O<br />

O<br />

O<br />

DMTMM<br />

4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-<br />

methylmorpholinium chloride<br />

O<br />

N<br />

N<br />

N<br />

N<br />

O<br />

Cl<br />

DMTr<br />

4,4’-dimethyltrityl<br />

DMTST<br />

(dimethylthio)methylsulfonium<br />

trifluoromethanesulfonate<br />

S<br />

S<br />

S<br />

O<br />

O<br />

S<br />

O<br />

F<br />

F<br />

F<br />

DNA deoxyribonucleic acid NA<br />

xxvi


TABLE <strong>OF</strong> CONTENTS<br />

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Abbreviation Chemical Name Chemical Structure<br />

DPA (DIPA)<br />

diisopropylamine<br />

N<br />

H<br />

DPBP 2,2'-bis(diphenylphosphino)biphenyl<br />

(S)<br />

Ph 2 P PPh 2<br />

O<br />

O<br />

DPDC diisopropyl peroxydicarbonate<br />

O O<br />

O<br />

O<br />

N -<br />

N +<br />

DPDM<br />

diphenyl diazomethane<br />

DPEDA<br />

1,2-diamino-1,2-diphenylethane<br />

H 2 N NH 2<br />

(R) (R)<br />

Ph<br />

DPIBF diphenylisobenzofuran<br />

O<br />

Ph<br />

DPPA<br />

diphenylphosphoryl azide (diphenylphosphorazidate)<br />

O O<br />

P<br />

O<br />

N N + N -<br />

Dppb (ddpb) 1,4-bis(diphenylphosphino)butane Ph 2 P<br />

PPh 2<br />

dppe<br />

1,2-bis(diphenylphosphino)ethane<br />

Ph 2 P<br />

PPh 2<br />

dppf 1,1'-bis(diphenylphosphino)ferrocene Fe<br />

PPh 2<br />

PPh 2<br />

dppm<br />

bis(diphenylphosphino)methane<br />

Ph 2 P PPh 2<br />

dppp<br />

1,3-bis(diphenylphosphino)propane<br />

Ph 2 P PPh 2<br />

DPS<br />

(also TBDPS or<br />

BPS)<br />

t-butyldiphenylsilyl<br />

Si<br />

xxvii


TABLE <strong>OF</strong> CONTENTS<br />

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Abbreviation Chemical Name Chemical Structure<br />

DPTC<br />

O,O’-di(2’-pyridyl)thiocarbonate<br />

N<br />

O<br />

S<br />

O<br />

N<br />

dr diastereomeric ratio NA<br />

O<br />

DTBAD (DBAD) di-tert-butyl azodicarboxylate N<br />

O N<br />

O<br />

O<br />

DTBB<br />

4,4’-di-tert-butylbiphenyl<br />

DTBP<br />

2,6-di-tert-butylpyridine<br />

N<br />

DTBMP<br />

2,6-di-tert-butyl-4-methylpyridine<br />

N<br />

DTE 1,4-dithioerythritol SH<br />

OH<br />

SH OH<br />

DVS<br />

1,3-divinyl-1,1,3,3-tetramethyldisiloxane<br />

Me Me<br />

O<br />

Si Si<br />

Me Me<br />

E +<br />

electrophile (denotes any electrophile in general)<br />

NA<br />

E2 bimolecular elimination NA<br />

ED effective dosage NA<br />

EDA<br />

ethyl diazoacetate<br />

O<br />

O<br />

N + N-<br />

EDDA<br />

ethylenediamine diacetate<br />

H 3 N<br />

OAc<br />

OAc<br />

NH 3<br />

EDC (EDAC)<br />

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide<br />

(ethyldimethylaminopropylcarbodiimide)<br />

N<br />

C<br />

N<br />

N<br />

EDCI<br />

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide<br />

hydrochloride<br />

N C N NH Cl<br />

PO 3 H 2<br />

EDCP<br />

2,3-bis-phosphonopentanedioic acid<br />

(ethylene dicarboxylic 2,3-diphosphonic acid)<br />

HOOC<br />

PO 3 H 2<br />

COOH<br />

EDG electron-donating group NA<br />

EDTA<br />

ethylenediamine tetraacetic acid<br />

HOOC<br />

HOOC<br />

N<br />

N<br />

COOH<br />

COOH<br />

xxviii


TABLE <strong>OF</strong> CONTENTS<br />

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Abbreviation Chemical Name Chemical Structure<br />

ee enantiomeric excess NA<br />

EE<br />

ethoxyethyl<br />

O<br />

E i intramolecular syn elimination NA<br />

en<br />

ethylenediamine<br />

H 2 N<br />

NH 2<br />

EOM ethoxymethyl O<br />

ESR electron spin resonance (spectroscopy) NA<br />

Et<br />

ethyl<br />

ETSA<br />

ethyl trimethylsilylacetate<br />

O<br />

O<br />

Si<br />

EVE ethyl vinyl ether O<br />

EWG electron-withdrawing group NA<br />

Fc ferrocenyl Fe<br />

FDP<br />

fructose-1,6-diphosphate<br />

H 2 O 3 POH 2 C<br />

H<br />

H<br />

HO<br />

O<br />

HO<br />

H<br />

OH<br />

CH 2 OPO 3 H 2<br />

F<br />

FDPP<br />

pentafluorophenyl diphenylphosphinate<br />

F<br />

F<br />

Ph<br />

O<br />

P O F<br />

Ph<br />

F<br />

Fl<br />

fluorenyl<br />

FMO frontier molecular orbital (theory) NA<br />

O<br />

Fmoc<br />

9-fluorenylmethoxycarbonyl<br />

O<br />

fod<br />

6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-<br />

octanedione<br />

F<br />

F<br />

F F O<br />

F F F<br />

O<br />

fp flash point NA<br />

FSM Mesoporous silica NA<br />

FTT 1-fluoro-2,4,6-trimethylpyridinium triflate N F S<br />

O<br />

O<br />

O<br />

F<br />

F<br />

F<br />

xxix


TABLE <strong>OF</strong> CONTENTS<br />

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Abbreviation Chemical Name Chemical Structure<br />

FVP flash vacuum pyrolysis NA<br />

GEBC gel entrapped base catalyst NA<br />

h hours (length of reaction time) NA<br />

hν irradiation with light NA<br />

HATU<br />

O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-<br />

tetramethyluronium hexafluorophosphate<br />

N<br />

PF 6<br />

O + N<br />

N N<br />

N<br />

N<br />

Het heterocycle NA<br />

O<br />

O<br />

hfacac hexafluoroacetylacetone F 3 C<br />

CF 3<br />

F<br />

F F<br />

F<br />

HFIP<br />

1,1,1,3,3,3-hexafluoro-2-propanol<br />

(hexafluoroisopropanol)<br />

F<br />

OH<br />

F<br />

HO<br />

HGK<br />

4-hydroxy-2-ketoglutarate<br />

O<br />

O<br />

O<br />

O<br />

O<br />

Hgmm millimeter of mercury (760 Hgmm = 1 atm = 760 Torr) NA<br />

HLE horse liver esterase NA<br />

Hmb<br />

2-hydroxy-4-methoxybenzyl<br />

O<br />

OH<br />

HMDS<br />

1,1,1,3,3,3-hexamethyldisilazane<br />

Si<br />

H<br />

N<br />

Si<br />

N<br />

HMPA<br />

hexamethylphosphoric acid triamide<br />

(hexamethylphosphoramide)<br />

N<br />

P<br />

O<br />

N<br />

N<br />

HMPT hexamethylphosphorous triamide N P<br />

N<br />

N<br />

HOAt 1-hydroxy-7-azabenzotriazole<br />

N<br />

N N<br />

OH<br />

N<br />

HOBt (HOBT) 1-hydroxybenzotriazole<br />

N<br />

N<br />

HOMO highest occupied molecular orbital NA<br />

OH<br />

HOSu<br />

N-hydroxysuccinimide<br />

O<br />

OH<br />

N<br />

O<br />

HPLC high-pressure liquid chromatography NA<br />

HWE Horner-Wadsworth-Emmons NA<br />

i iso NA<br />

xxx


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

IBA 2-iodosobenzoic acid O<br />

O<br />

I<br />

HO<br />

O<br />

IBX<br />

o-iodoxybenzoic acid<br />

HO<br />

O<br />

I<br />

O<br />

IDCP<br />

bis(2,4,6-collidine)iodonium perchlorate<br />

N I + N ClO 4 -<br />

Imid (Im)<br />

imidazole<br />

HN<br />

N<br />

INOC intramolecular nitrile oxide cycloaddition NA<br />

IPA isopropyl alcohol HO<br />

Ipc<br />

isopinocamphenyl<br />

H<br />

IR infrared spectroscopy NA<br />

K-10 a type of Montmorillonite clay NA<br />

KDA<br />

potassium diisopropylamide<br />

N<br />

K<br />

K<br />

KHMDS<br />

potassium bis(trimethylsilyl)amide<br />

N<br />

Si Si<br />

KSF a type of Montmorillonite clay NA<br />

L ligand NA<br />

L.R.<br />

Lawesson’s reagent (2,4-bis-(4-methoxyphenyl)-<br />

[1,3,2,4]dithiadiphosphetane 2,4-dithion)<br />

MeO<br />

S<br />

P<br />

S<br />

S<br />

P<br />

S<br />

OMe<br />

LA Lewis acid NA<br />

LAB lithium amidotrihydroborate LiH 2 NBH 3<br />

LAH<br />

lithium aluminum hydride<br />

LiAlH 4<br />

LD 50<br />

dose that is lethal to 50% of the test subjects (cells,<br />

animals, humans etc.)<br />

NA<br />

LDA<br />

lithium diisopropylamide<br />

N<br />

Li<br />

LDBB lithium 4,4’-t-butylbiphenylide Li<br />

xxxi


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

LDE lithium diethylamide Li<br />

N<br />

LDPE<br />

lithium perchlorate-diethyl etherate<br />

LiClO 4 - Et 2 O<br />

LHMDS<br />

(LiHMDS)<br />

lithium bis(trimethylsilyl)amide<br />

Li<br />

N<br />

Si Si<br />

LICA<br />

lithium isopropylcyclohexylamide<br />

Li<br />

N<br />

BuLi - KOt-Bu<br />

LICKOR (super<br />

butyllithium-potassium tert-butoxide<br />

base)<br />

liq. liquid NA<br />

LiTMP<br />

(LTMP)<br />

lithium 2,2,6,6-tetramethylpiperidide<br />

N<br />

Li<br />

LPT<br />

lithium pyrrolidotrihydroborate<br />

(lithium pyrrolidide-borane)<br />

Li(CH 2 ) 4 NBH 3<br />

L-selectride<br />

lithium tri-sec-butylborohydride<br />

BH<br />

Li<br />

LTA<br />

lead tetraacetate<br />

Pb(OAc) 4<br />

LUMO lowest unoccupied molecular orbital NA<br />

lut<br />

2,6-lutidine<br />

N<br />

m meta NA<br />

MA<br />

maleic anhydride<br />

O<br />

O<br />

O<br />

MAD<br />

methyl aluminum bis(2,6-di-t-butyl-4-<br />

methylphenoxide)<br />

O<br />

AlMe<br />

2<br />

MAT methyl aluminum bis(2,4,6-tri-t-butylphenoxide) O AlMe<br />

2<br />

xxxii


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

MBT<br />

2-mercaptobenzothiazole<br />

HS<br />

S<br />

N<br />

COOOH<br />

m-CPBA<br />

meta chloroperbenzoic acid<br />

Cl<br />

Me<br />

methyl<br />

CH 3<br />

MEM (2-methoxyethoxy)methyl<br />

O<br />

O<br />

MEPY<br />

methyl 2-pyrrolidone-5(S)-carboxylate<br />

O<br />

O<br />

H<br />

N<br />

O<br />

Mes<br />

mesityl<br />

HO<br />

mesal<br />

N-methylsalicylaldimine<br />

N<br />

MIC methyl isocyanate O C N<br />

MMPP<br />

(MMPT)<br />

magnesium monoperoxyphthalate<br />

Mg 2+<br />

O<br />

O<br />

O<br />

O<br />

O<br />

MOM<br />

methoxymethyl<br />

oxodiperoxomolybdenum(pyridine)-<br />

NA<br />

MoOPH<br />

(hexamethylphosphoric triamide)<br />

mp melting point NA<br />

MPa<br />

megapascal = 10 6 Pa = 10 atm (pressure)<br />

O<br />

MPD<br />

(NMP)<br />

N-methyl-2-pyrrolidinone<br />

N<br />

O<br />

O<br />

MPM methoxy(phenylthio)methyl S<br />

MPM<br />

(PMB)<br />

p-methoxybenzyl<br />

O<br />

xxxiii


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

Cl<br />

MPPC<br />

N-methyl piperidinium chlorochromate<br />

O<br />

Cr<br />

O<br />

O<br />

NH<br />

O<br />

Ms<br />

mesyl (methanesulfonyl)<br />

S<br />

O<br />

CH 3<br />

MS mass spectrometry NA<br />

MS molecular sieves NA<br />

O<br />

MSA<br />

methanesulfonic acid<br />

HO<br />

S<br />

O<br />

CH 3<br />

MSH<br />

o-mesitylenesulfonyl hydroxylamine<br />

HO<br />

H O<br />

N<br />

S<br />

O<br />

MSTFA<br />

N-methyl-N-(trimethylsilyl) trifluoroacetamide<br />

F<br />

F<br />

F<br />

O<br />

Si<br />

N<br />

MTAD N-methyltriazolinedione O<br />

N<br />

O<br />

N N<br />

MTEE<br />

(MTBE)<br />

methyl t-butyl ether<br />

O<br />

MTM<br />

MTO<br />

methylthiomethyl<br />

methyltrioxorhenium<br />

S<br />

O<br />

O Re CH 3<br />

O<br />

Me Me<br />

O<br />

Mtr (4-methoxy-2,3,6-trimethylphenyl)sulfonyl<br />

S<br />

OMe<br />

O<br />

Me<br />

MVK<br />

methyl vinyl ketone<br />

O<br />

mw microwave NA<br />

n normal (e.g. unbranched alkyl chain) NA<br />

H<br />

H<br />

O<br />

NH 2<br />

O<br />

O<br />

N<br />

NADPH<br />

nicotinamide adenine dinucleotide phosphate<br />

OH OH<br />

N<br />

NH 2<br />

N<br />

O<br />

P O<br />

OH<br />

O<br />

P O<br />

OH<br />

N N<br />

O<br />

O<br />

OH O P OH<br />

OH<br />

xxxiv


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

NaHMDS<br />

sodium bis(trimethylsilyl)amide<br />

Na<br />

N<br />

Si Si<br />

Naph<br />

(Np)<br />

naphthyl<br />

O<br />

NBA<br />

N-bromoacetamide<br />

Br<br />

N<br />

H<br />

NBD<br />

(nbd)<br />

norbornadiene<br />

O<br />

NBS<br />

N-bromosuccinimide<br />

N<br />

Br<br />

O<br />

O<br />

NCS<br />

N-chlorosuccinimide<br />

N<br />

Cl<br />

O<br />

N f nonafluorobutanesulfonyl<br />

S<br />

O<br />

O<br />

F<br />

F<br />

F<br />

F<br />

F<br />

F<br />

F<br />

F<br />

F<br />

O<br />

NHPI<br />

N-hydroxyphthalimide<br />

N<br />

OH<br />

O<br />

NIS N-iodosuccinimide O<br />

N<br />

O<br />

I<br />

NMM N-methylmorpholine N O<br />

NMO<br />

N-methylmorpholine oxide<br />

O<br />

N<br />

O<br />

O<br />

NMP N-methyl-2-pyrrolidinone N<br />

NMR nuclear magnetic resonance NA<br />

NORPHOS<br />

bis(diphenylphosphino)bicyclo[2.2.1]-hept-5-ene<br />

Ph 2 P PPh 2<br />

Nos 4-nitrobenzenesulfonyl<br />

S<br />

O<br />

O<br />

N<br />

O<br />

O<br />

xxxv


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

O<br />

NPM<br />

N-phenylmaleimide<br />

N<br />

O<br />

NR no reaction NA<br />

Ns<br />

2-nitrobenzenesulfonyl<br />

O<br />

O<br />

S<br />

O<br />

O<br />

N<br />

NSAID non steroidal anti-inflammatory drug NA<br />

Nuc nucleophile (general) NA<br />

o ortho NA<br />

Oxone<br />

potassium peroxymonosulfate<br />

p para NA<br />

KHSO 5<br />

PAP<br />

2,8,9-trialkyl-2,5,8,9-tetraaza-<br />

1-phospha-bicyclo[3.3.3]undecane<br />

R<br />

N<br />

P<br />

N<br />

N<br />

R<br />

R<br />

N<br />

PBP<br />

pyridinium bromide perbromide<br />

N<br />

H<br />

Br 3<br />

PCC<br />

pyridinium chlorochromate<br />

N<br />

H<br />

O<br />

O Cr<br />

O<br />

Cl<br />

PDC<br />

pyridinium dichromate<br />

N<br />

H<br />

O<br />

Cr<br />

O O<br />

O<br />

O<br />

Cr O<br />

O<br />

N<br />

H<br />

PEG polyethylene glycol NA<br />

Ph<br />

Pf<br />

9-phenylfluorenyl<br />

pfb<br />

perfluorobutyrate<br />

F<br />

F<br />

F<br />

F<br />

F<br />

F<br />

O<br />

F<br />

O<br />

Ph<br />

phenyl<br />

PHAL phthalazine N<br />

N<br />

phen<br />

9,10-phenanthroline<br />

N N<br />

xxxvi


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

Phth<br />

phthaloyl<br />

O<br />

C<br />

C<br />

O<br />

pic<br />

2-pyridinecarboxylate<br />

O<br />

O<br />

N<br />

O<br />

PIDA<br />

(BAIB or DIB)<br />

phenyliodonium diacetate<br />

O<br />

I<br />

O<br />

O<br />

PIFA<br />

phenyliodonium bis(trifluoroacetate)<br />

F 3 C<br />

O<br />

O<br />

I<br />

O<br />

O<br />

CF 3<br />

Piv pivaloyl O<br />

PLE pig liver esterase NA<br />

PMB<br />

(MPM)<br />

p-methoxybenzyl<br />

O<br />

PMP 4-methoxyphenyl O<br />

PMP<br />

1,2,2,6,6-pentamethylpiperidine<br />

Me<br />

Me<br />

N<br />

Me<br />

Me<br />

Me<br />

PNB<br />

p-nitrobenzyl<br />

O<br />

N<br />

O<br />

PNZ<br />

p-nitrobenzyloxycarbonyl<br />

O<br />

N<br />

O<br />

O<br />

O<br />

PPA<br />

polyphosphoric acid<br />

NA<br />

PPI<br />

2-phenyl-2-(2-pyridyl)-2H-imidazole<br />

N<br />

N<br />

N<br />

PPL pig pancreatic lipase NA<br />

PPO 4-(3-phenylpropyl)pyridine-N-oxide O N Ph<br />

PPSE polyphosphoric acid trimethylsilyl ester NA<br />

xxxvii


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

O<br />

PPTS<br />

pyridinium p-toluenesulfonate<br />

S<br />

O<br />

O<br />

N<br />

H<br />

Pr<br />

propyl<br />

psi pounds per square inch NA<br />

PT 1-phenyl-1H-tetrazol-yl N<br />

P.T. proton transfer NA<br />

Ph<br />

N<br />

N<br />

N<br />

PTAB phenyltrimethylammonium perbromide N Br 3<br />

PTC Phase transfer catalyst NA<br />

PTMSE<br />

(2-phenyl-2-trimethylsilyl)ethyl<br />

Si<br />

PTSA<br />

(or TsOH) p-toluenesulfonic acid HO 3 S<br />

CH 3<br />

PVP poly(4-vinylpyridine) NA<br />

Py<br />

pyridine<br />

(pyr)<br />

N<br />

r.t. room temperature NA<br />

rac racemic NA<br />

NH 2<br />

RAMP<br />

(R)-1-amino-2-(methoxymethyl)pyrrolidine<br />

N<br />

(R)<br />

O<br />

RaNi Raney nickel NA<br />

RB Rose Bengal See Rose bengal<br />

RCAM ring-closing alkyne metathesis NA<br />

RCM ring-closing metathesis NA<br />

Rds (or RDS) rate-determining step NA<br />

Red-Al<br />

sodium bis(2-methoxyethoxy) aluminum hydride<br />

O<br />

O<br />

O<br />

Al H<br />

H<br />

O<br />

Na<br />

Rham<br />

rhamnosyl<br />

H<br />

O Me<br />

O<br />

O<br />

O<br />

H<br />

H<br />

R f perfluoroalkyl group<br />

C n F 2n+1<br />

R f retention factor in chromatography NA<br />

ROM ring-opening metathesis NA<br />

ROMP ring-opening metathesis polymerization NA<br />

xxxviii


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

Rose Bengal<br />

(RB)<br />

2,4,5,7-tetraiodo-3',4',5',6'-tetrachlorofluorescein<br />

disodium salt<br />

(a photosensitizer)<br />

O<br />

I<br />

I<br />

Cl<br />

O<br />

I<br />

O<br />

I<br />

COO<br />

2 Na<br />

Cl<br />

Cl<br />

Cl<br />

s seconds (length of reaction time) NA<br />

PPh 2<br />

S,S,-chiraphos (S,S)-2,3-bis(diphenylphosphino)butane<br />

(S)<br />

(S)<br />

PPh 2<br />

Salen<br />

N,N’-ethylenebis(salicylideneiminato)<br />

bis(salicylidene)ethylenediamine<br />

N<br />

OH<br />

N<br />

HO<br />

salophen o-phenylenebis(salicylideneiminato) N N<br />

OH<br />

HO<br />

SAMP (S)-1-amino-2-(methoxymethyl)pyrrolidine<br />

N<br />

NH 2<br />

O<br />

SC CO 2 supercritical carbon-dioxide NA<br />

SDS<br />

sodium dodecylsulfate<br />

O<br />

O Na<br />

S O<br />

O<br />

sec secondary NA<br />

SEM 2-(trimethylsilyl)ethoxymethyl<br />

O<br />

Si<br />

SES 2-[(trimethylsilyl)ethyl]sulfonyl<br />

Si<br />

O<br />

S<br />

O<br />

SET single electron transfer NA<br />

Sia<br />

1,2-dimethylpropyl (secondary isoamyl)<br />

SPB sodium perborate Na BO 3<br />

xxxix


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

TADDOL<br />

2,2-dimethyl-α,α,α 1 , α 1 -tetraaryl-1,3-dioxolane-4,5-<br />

dimethanol<br />

O<br />

O<br />

OH<br />

H Ar<br />

(R)<br />

(R)<br />

Ar<br />

Ar<br />

H Ar<br />

OH<br />

NEt 2<br />

TASF<br />

tris(diethylamino)sulfonium difluorotrimethylsilicate<br />

Et 2 N<br />

S<br />

NEt 2<br />

SiMe 3 F 2<br />

TBAB<br />

tetra-n-butylammonium bromide<br />

N<br />

Br<br />

TBAF tetra-n-butylammonium fluoride Bu 4 N F<br />

TBAI tetra-n-butylammonium iodide Bu 4 N I<br />

Br<br />

TBCO<br />

tetrabromocyclohexadienone<br />

Br<br />

Br<br />

Br<br />

O<br />

TBDMS<br />

(TBS)<br />

t-butyldimethylsilyl<br />

Si<br />

TBDPS<br />

(BPS)<br />

t-butyldiphenylsilyl<br />

Si<br />

O<br />

TBH tert-butyl hypochlorite Cl<br />

TBHP tert-butyl hydroperoxide<br />

O<br />

OH<br />

TBP<br />

tributylphosphine<br />

P<br />

TBT 1-tert-butyl-1H-tetrazol-5-yl N<br />

t-Bu<br />

N<br />

N<br />

N<br />

TBTH<br />

tributyltin hydride<br />

H<br />

Sn<br />

TBTSP<br />

t-butyl trimethylsilyl peroxide<br />

O<br />

Si O<br />

xl


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

TCCA trichloroisocyanuric acid<br />

Cl N<br />

O<br />

O<br />

Cl<br />

N<br />

N<br />

Cl<br />

O<br />

S<br />

TCDI<br />

thiocarbonyl diimidazole<br />

N<br />

N<br />

N<br />

N<br />

N<br />

N<br />

TCNE<br />

tetracyanoethylene<br />

N<br />

N<br />

TCNQ<br />

7,7,8,8-tetracyano-para-quinodimethane<br />

NC<br />

NC<br />

CN<br />

CN<br />

TDS<br />

dimethyl thexylsilyl<br />

Si<br />

TEA triethylamine N<br />

TEBACl benzyl trimethylammonium chloride N<br />

Cl<br />

TEMPO<br />

2,2,6,6-tetramethyl-1-piperidinyloxy free radical<br />

N<br />

O•<br />

Teoc<br />

2-(trimethylsilyl)ethoxycarbonyl<br />

O<br />

O<br />

Si<br />

TEP<br />

triethylphosphite<br />

O<br />

P<br />

O<br />

O<br />

TES triethylsilyl Si<br />

Tf<br />

trifluoromethanesulfonyl<br />

F<br />

F<br />

F<br />

O<br />

S<br />

O<br />

TFA<br />

trifluoroacetic acid<br />

F<br />

F<br />

F<br />

OH<br />

O<br />

Tfa<br />

trifluoroacetamide<br />

F<br />

F<br />

F<br />

NH 2<br />

O<br />

xli


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

TFAA<br />

trifluoroacetic anhydride<br />

F<br />

F<br />

F<br />

O<br />

O<br />

O<br />

F<br />

F<br />

F<br />

TFE<br />

2,2,2-trifluoroethanol<br />

F<br />

F<br />

F<br />

OH<br />

TFMSA<br />

trifluoromethanesulfonic acid<br />

(triflic acid)<br />

F<br />

F<br />

F<br />

O<br />

S<br />

O<br />

OH<br />

TFP<br />

tris(2-furyl)phosphine<br />

O<br />

P<br />

O<br />

O<br />

Th<br />

2-thienyl<br />

S<br />

thexyl<br />

1,1,2-trimethylpropyl<br />

THF<br />

tetrahydrofuran<br />

O<br />

THP 2-tetrahydropyranyl O<br />

TIPB<br />

1,3,5-triisopropylbenzene<br />

TIPS triisopropylsilyl Si<br />

TMAO (TMANO) trimethylamine N-oxide<br />

N + O -<br />

TMEDA<br />

N,N,N',N'-tetramethylethylenediamine<br />

N<br />

N<br />

TMG<br />

1,1,3,3-tetramethylguanidine<br />

N<br />

NH<br />

N<br />

TMGA<br />

tetramethylguanidinium azide<br />

N<br />

N<br />

NH 2<br />

N 3<br />

xlii


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

O<br />

Tmob<br />

2,4,6-trimethoxybenzyl<br />

O<br />

O<br />

TMP<br />

2,2,6,6-tetramethylpiperidine<br />

N<br />

H<br />

TMS trimethylsilyl<br />

Si<br />

TMSA trimethylsilyl azide Si<br />

N<br />

N<br />

+<br />

N -<br />

TMSEE<br />

(trimethylsilyl)ethynyl ether<br />

Si<br />

O<br />

Si<br />

TMU<br />

tetramethylurea<br />

N<br />

O<br />

N<br />

TNM<br />

tetranitromethane<br />

-<br />

O<br />

-<br />

O<br />

N +<br />

O<br />

-<br />

O<br />

N O + O<br />

N +<br />

N + O -<br />

O<br />

Tol<br />

p-tolyl<br />

tolbinap<br />

2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl<br />

P<br />

P<br />

2<br />

2<br />

TPAP<br />

tetra-n-propylammonium perruthenate<br />

N<br />

O<br />

O Ru O<br />

O<br />

TPP<br />

triphenylphosphine<br />

P<br />

Ph<br />

TPP<br />

5,10,15,20-tetraphenylporphyrin<br />

Ph<br />

NH<br />

N<br />

N<br />

HN<br />

Ph<br />

Ph<br />

xliii


TABLE <strong>OF</strong> CONTENTS<br />

SEARCH TEXT<br />

Abbreviation Chemical Name Chemical Structure<br />

TPS triphenylsilyl Si<br />

Tr trityl (triphenylmethyl) C<br />

O<br />

Trisyl 2,4,6-triisopropylbenzenesulfonyl S<br />

O<br />

Troc<br />

2,2,2-trichloroethoxycarbonyl<br />

O<br />

O<br />

Cl<br />

Cl<br />

Cl<br />

TS transition state (or transition structure) NA<br />

Ts (Tos)<br />

p-toluenesulfonyl<br />

O<br />

S<br />

O<br />

TSE (TMSE) 2-(trimethylsilyl)ethyl Si<br />

TTBP<br />

2,4,5-tri-tert-butylpyrimidine<br />

N<br />

N<br />

TTMSS tris(trimethylsilyl)silane Si SiH<br />

Si<br />

Si<br />

TTN<br />

thallium(III)-trinitrate<br />

Tl(NO 3 ) 3<br />

UHP<br />

urea-hydrogen peroxide complex<br />

H 2<br />

N<br />

O<br />

NH 2<br />

H 2 O 2<br />

Vitride<br />

(Red-Al)<br />

sodium bis(2-methoxyethoxy)aluminum hydride<br />

O<br />

O<br />

O<br />

Al H<br />

H<br />

Na<br />

O<br />

wk weeks (length of reaction time) NA<br />

Z (Cbz)<br />

benzyloxycarbonyl<br />

O<br />

O<br />

xliv

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