Accoun ts Letters - Thieme Chemistry

1181
Insoluble Polymer-Bound (IPB) Approach to the
Catalytic Asymmetric Dihydroxylation of Alkenes
P. Salvadori, D. Pini, A. Petri
1191
Iodocarbocyclization and Iodoaminocyclization
Reactions Mediated by a Metallic Reagent
O. Kitagawa, T. Taguchi
1200
Facile Acetylation of Alcohols, Ethers and Ketals
with Catalytic FeCl3 in AcOH
G. V. M. Sharma*, A. K. Mahalingam, M. Nagarajan, A. Ilangovan,
P. Radhakrishna
1203
Preparation of Non-Symmetrical 2,3-Bis-(2,2’-oligopyridyl)pyrazines
via 1,2-Disubstituted Ethanones
F. R. Heirtzler
1207
Copper(II) Pivalate/Oxone: An Improved Promoter
System for Aryl Transfer via Organo-Bismuth
Reagents
G. S. Sheppard
Accounts and
Rapid Communications in
Synthetic Organic Chemistry
R 1
NuH MLn ( ) n
Me
N CO2R3 n
NuMLn-1 ( ) n I2
"activation of nucleophile"
"control of selectivity "
N
m
R 2
N
N
I
N
N R1 m
n
1999
No. 8
August
( )n
R 2
Nu
Accounts
Letters

Letters
IV Table of Contents
1211
Kinetic and Thermodynamic Control in the
Synthesis of Tetrahydro-Pyrans and -Furans from
1,4-Diols by Stereospecific Phenylsulfanyl (PhS)
Migration: Competition Between exo and endo
Transition States and between [1,2] and [1,4]
Sulfanyl Participation
J. Eames, N. Kuhnert, F. H. Sansbury, S. Warren
1215
[1,4]-SPh Shift Cyclisations or [1,2]-SPh-Cyclisations
as Alternative Cascade Sequences for Stereocontrolled
Synthesis of Substituted Tetrahydrofurans
J. Eames, N. Kuhnert, S. Warren
1219
Synthesis of a Polyhydroxyquinolizidine bearing a
Polyhydroxylated Carbon Side-Chain
C. Schaller, P. Vogel
1223
Palladium-Catalyzed Synthesis of N-Aryl- and N-
Heteroaryl-aza-crown Ethers via Cross-Coupling
Reactions of Aryl- and Heteroaryl Bromides with
Aza-crown Ethers
B. Witulski
1227
First Synthesis of Xerulin, an Inhibitor of the
Biosynthesis of Cholesterol
K. Siegel, R. Brückner
1231
Oxidative Asymmetrization of Racemic Alkenes:
Asymmetric Synthesis of Optically Active Dicyclopentadiene
Derivatives
Y. Kohmura, T. Katsuki
O
Ph3P
+
(4 eq)
O
O
H
H
1) PhCO3Bu-t (1 eq)
Cu(OTf)2-L* (0.05 eq)
2) NaOHaq O
O
H
H
HO
(racemic)
L* = chiral tris(oxazoline) ligand
80% ee, 27%
O
O
O
O

Table of Contents V
1235
Formation of Four-Membered Rings Using the
Intramolecular Wittig Reaction: Convenient
Generation of Functionalised Butadienes
R. A. Aitken, M. E. Balkovich, H. J. Bestmann, O. Clem,
S. E. Gibson, T. Röder
1237
A Convenient and Practical Route to Novel a-Allenic
Ketones through a Wittig Reaction
K. Kumar, S. Kaur, M. P. S. Ishar
1239
The Synthesis of Aminoazole Analogs of Lysine and
Arginine: The Mitsunobu Reaction with Lysinol and
Argininol
H.-O. Kim, M. Kahn
1241
A Concise Synthesis of 3-Hydroxy-4-(b-glucopyranosyl)
Benzoate: A New Route to b-C-Aryl
Glycosides
C. Fuganti, S. Serra
1243
Formal Protection of Vinylepoxides via Stereospecific
Chlorohydrin Formation
N. Daviu, A. Delgado, A. Llebaria
1245
A Convenient New Method for the Bromination of
Deactivated Aromatic Compounds
J. Duan, L. H. Zhang, W. R. Dolbier, Jr.
Ph 3P
O
OR 1
O R 2
R 1 O
R 2
O
R 1 O
O
R 2
Letters

Letters
VI Table of Contents
1247
Deprotection of Tetrahydropyranyl Ethers with
Montmorillonite K-10 Clay in Methanol
T. Taniguchi, K. Kadota, A. S. ElAza, K. Ogasawara
1249
a-Keto Esters as Electrophiles for the Chalcogeno-
Baylis-Hillman Reaction
D. Basavaiah, K. Muthukumaran, B. Sreenivasulu
1251
Microwave Assisted Synthesis of Pyrrolo[2,1c][1,4]benzodiazepine-5,11-diones
A. Kamal, B. S. N. Reddy, G. S. K. Reddy
1253
1,4-Addition Reactions of Bis(iodozincio)methane
with a,b-Unsaturated Ketones
S. Matsubara, D. Arioka, K. Utimoto
1255
Esterification of Carboxylic Acids with Alcohols by
4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium
Chloride (DMTMM)
M. Kunishima, J. Morita, C. Kawachi, F. Iwasaki, K. Terao,
S. Tani
1257
Diastereoselective Oxyselenylation of 1,n-Diolefins
Utilizing PET Generated [PhSeSePh] +. as an Electrophilic
Species: An Efficient and General Strategy
for the Synthesis of a,a’-trans-Dialkyl Cyclic Ethers
G. Pandey, R. Sochanchingwung, S. K. Tiwari
R 1
O
OH
+
MeO
N
MeO
N
N
N
+ Me
O
Cl- DMTMM
MeN
R2OH rt
O
R 1
O
OR 2

Table of Contents VII
1259
Unexpected Switching between Addition and Substitution
in the Rhodium-Catalysed Reaction between
Tin Hydrides and Propargyl Ethers
T. N. Mitchell, S.-N. Moschref
1261
Lithium Tetrafluoroborate-in Acetonitrile ( LTAN )
Catalyzed Ferrier Rearrangement – Facile Synthesis
of Alkyl 2,3-Unsaturated Glycopyranosides
B Sobhana Babu, K. K. Balasubramanian
1263
First Synthesis of 1-Phenyl-3-pyrrol-1-ylindan-2carboxylic
Acid, a New Scaffold of Potential Nonpeptide
Endothelin Receptor Antagonists
J. Guillon, P. Dallemagne, S. Stiebing, P. R. Bovy, S. Rault
1265
Iminophosphoranes in Heterocyclic Chemistry.
A Simple One-Pot Synthesis of Dihydropyrimidines
and Pyrimidines
E. Rossi, G. Abbiati, E. Pini
1268
A Practical Transformation of Aldehydes into (E)-
Iodoalkenes with Geminal Dichromium Reagents
K. Takai, T. Ichiguchi, S. Hikasa
1271
A New Synthesis of Pyrrole-2-Carboxylic Acids
C. S. Pak, M. Nyerges
Letters

Letters
VIII Table of Contents
1274
A Facile Synthesis of 3’-Deoxy-3’-fluorothymidine
via a Highly Stereoselective Glycosylation with 2,3-
Dideoxy-3-fluoro-D-erythro-pentofuranosyl Diethyl
Phosphite
J. Inagaki, H. Sakamoto, M. Nakajima, S. Nakamura,
S. Hashimoto
1277
Polymer-Supported Acid Catalyst in the Carbon-
Carbon Bond Formation of Acetals with Silylated
Nucleophiles
N. Tanaka, Y. Masaki
1280
Treatment of N-Boc Derivatives of b-Amino Alcohols
with N,N-Diethylaminosulfur Trifluoride Leads to
Chiral Oxazolidinones: An Unexpected Intramolecular
Cyclization
H. Zhao, A. Thurkauf
1283
A New and Extremely Active Corey’s Chiral Oxazaborolidine
Catalyst
K. Ishihara, S. Kondo, H. Yamamoto
1286
Sulfur-Controlled Exo Selective Aryl Radical
Cyclization onto Exo-Methylenecycloalkanes
H. Ishibashi, T. Kobayashi, D. Takamasu
1289
A Novel Carbocyclic Ring Closure of Hex-5enopyranosides
and Pent-4-enofuranosides
J. K. Gallos, T. V. Koftis, A. E. Koumbis, V. I. Moutsos
OTMS
O
N
Me
HN
Me
BzO
O
TMSO N
(1.5 equiv.)
BzO
F
OP(OEt)2 TMSOTf (1.0 equiv.)
EtCN, -50 °C, 30 min
α:β=64:36
R OMe
OMe
(50 mg)
NC
NC
O
O
N
O Ot DAST
CH2F Bu
O
O
O
O
polymer cat. (50 mg), TMS-Nu (1.5 eq.)
CH 3CN, reflux
R = aryl, aliphatic, α,β-unsaturated
Nu = CN, CH2COPh, CH2CO-2-Furyl
N
O Ot CH2OH DAST
Bu
SPh PhS
Br
Bu3SnH AIBN
( )n
( ) n
O
O
N
F
β:α=91:9
R OMe
Nu
N O
O

Table of Contents IX
1292
Highly Enantioselective Synthesis of Substituted
Piperidines using the Chiral Lithium Amide Base
Approach
N. J. Goldspink, N. S. Simpkins, M. Beckmann
1295
Chemistry of Insect Antifeedants from Azadirachta
indica (Part 22): Functionalisation of the Decalin
Fragment of Azadirachtin via a Claisen Rearrangement
Reaction
S. V. Ley, C. E. Gutteridge, A. R. Pape, C. D. Spilling,
C. Zumbrunn
1298
The Baker’s Yeast Reduction of the b-Keto Aldehydes
in the Presence of a Sulfur Compound
R. Hayakawa, M. Shimizu
1301
N-Carboalkoxy-2-Nitrobenzenesulfonamides:
A Practical Preparation of N-Boc-, N-Alloc-, and
N-Cbz-Protected Primary Amines
T. Fukuyama, M. Cheung, T. Kan
1304
Triazenes: A Useful Protecting Strategy for Sensitive
Secondary Amines
R. Lazny, J. Poplawski, J. Köbberling, D. Enders, S. Bräse
1307
Diastereoselectivity in Michael Additions to a
Pyrrolidinyl Enone
R. W. Bates, P. Kongsaeree
MeO2C
TESO
MeO2C R 1
N CO2Me
Bn
H
O
Ph
MeO2C TESO
O OBnR2
O
Ph
N
Li
Ph
N
Li Ph
THF, -78 °C
electrophile
(≥ 98% ee)
R 1
O OH
H
R2 R1 O
OH
R2 R1 OH
R2 Baker's Yeast
Sulfur-Compound
N
O Ot DAST
CH2F Bu
∆
MeO 2C
TESO
MeO2C H
O
N CO2Me
Bn E
MeO2C
TESO
O OBn
R2 R
OH
1
N
O Ot CH2OH DAST
Bu
OH
R 2
O
OH
N O
O
R 1
Letters

Letters
X Table of Contents
1310
Improved Method for the Preparation of
Macrocyclic Diamides
D. T. Gryko, D. Gryko, J. Jurczak
1313
Stereoselective Conjugate Addition of Alkyl Groups
to (S)-4-(tert-Butyldimethylsilyloxy)-2-phenylsulfonyl-2-cyclopentenone
by Means of Trialkylaluminum
Reagents
T. Yakura, K. Tanaka, M. Iwamoto, M. Nameki, M. Ikeda
1316
A New Route to L-Iduronate Building-blocks for the
Synthesis of Heparin-like Oligosaccharides
R. Ojeda, J. L. de Paz, M. Martín-Lomas, J. M. Lassaletta
1319
Novel Axial Chiral Sulfur-oxazoline Ligands with a
Biphenyl Backbone
Y. Imai, W. Zhang, T. Kida, Y. Nakatsuji, I. Ikeda
1322
A Concise Route to Carbasugars
Y. Le Merrer, C. Gravier-Pelletier, W. Maton, M. Numa,
J.-C. Depezay
1325
Synthetic Studies towards Mniopetals (I). A Short
Synthesis of a Key Intermediate for the Total
Synthesis of Mniopetals
J. Jauch
O
O
S
H2N OMe
+
OMe
TBDMSO
HO
O
O
H 2N
O
O
O
O
O
MeOH, NaOMe
48 h
O
NH
O
S
HN
O
57%
O
O
O
NH
O
HN
O
+ S
S
O
NH
O
HN
O
O
O
TBDMSO R
10%
SO2Ph R3Al SO2Ph toluene
OBn
O
MeO2C O
5 Steps, 17% overall
R
N M
SR' M RS'
N
R M
O
O
(S,aS )
3
M=PdCl2
RS'
O O
H H
M
(S,aR)
not found
Up to 82% ee was attained in palladium-catalyzed allylic
alkylation.
N
O
R
OTDS
PO OP
PO
PO
O
*
OP
+
*
O
S S
Si
SiO
*
S
*
S
OH SiO
+
*
S
*
S
OP
OH
Si = TBDMS

Table of Contents XI
1328
Organic Synthesis Supported by Antibody Catalysis
J. Hasserodt
1339
Indium
Compiled by Dramane Lainé
Errata 1340
New Tools
in Synthesis
Synlett
Spotlight

XII Table of Contents
Author Index
Abbiati, G. 1265
Aitken, R. A. 1235
Arioka, D. 1253
Balasubramanian, K. K. 1261
Balkovich, M. E. 1235
Basavaiah, 1249
Bates, R. W. 1307
Beckmann, M. 1292
Bestmann, H. J. 1235
Bovy, P. R. 1263
Bräse, S. 1304
Brückner, R. 1227
Cheung, M. 1301
Clem, O. 1235
Dallemagne, P. 1263
Daviu, N. 1243
de Paz, J. L. 1316
Delgado, A. 1243
Depezay, J.-C. 1322
Dolbier, Jr., W. R. 1245
Duan, J. 1245
Eames, J. 1211, 1215
ElAza, A. S. 1247
Enders, D. 1304
Fuganti, C. 1241
Fukuyama, T. 1301
Gallos, J. K. 1289
Gibson, S. E. 1235
Goldspink, N. J. 1292
Gravier-Pelletier, C. 1322
Gryko, D. 1310
Gryko, D. T. 1310
Guillon, J. 1263
Gutteridge, C. E. 1295
Hashimoto, S. 1274
Hasserodt, J. 1328
Hayakawa, R. 1298
Heirtzler, F. R. 1203
Hikasa, S. 1268
Ichiguchi, T. 1268
Ikeda, I. 1319
Ikeda, M. 1313
Ilangovan, A. 1200
Imai, Y. 1319
Inagaki, J. 1274
Ishar, M. P. S. 1237
Ishibashi, H. 1286
Ishihara, K. 1283
Iwamoto, M. 1313
Iwasaki, F. 1255
Jauch, J. 1325
Jurczak, J. 1310
Kadota, K. 1247
Kahn, M. 1239
Kamal, A. 1251
Kan, T. 1301
Katsuki, T. 1231
Kaur, S. 1237
Kawachi, C. 1255
Kida, T. 1319
Kim, H.-O. 1239
Kitagawa, O. 1191
Kobayashi, T. 1286
Köbberling, J. 1304
Koftis, T. V. 1289
Kohmura, Y. 1231
Kondo, S. 1283
Kongsaeree, P. 1307
Koumbis, A. E. 1289
Kuhnert, N. 1211, 1215
Kumar, K. 1237
Kunishima, M. 1255
Lainé, D. 1339
Lassaletta, J. M. 1316
Lazny, R. 1304
Le Merrer, Y. 1322
Ley, S. V. 1295
Llebaria, A. 1243
Mahalingam, A. K. 1200
Martín-Lomas, M. 1316
Masaki, Y. 1277
Maton, W. 1322
Matsubara, S. 1253
Mitchell, T. N. 1259
Morita, J. 1255
Moschref, S.-N. 1259
Moutsos, V. I. 1289
Muthukumaran, K. 1249
Nagarajan, M. 1200
Nakajima, M. 1274
Nakamura, S. 1274
Nakatsuji, Y. 1319
Nameki, M. 1313
Numa, M. 1322
Nyerges, M. 1271
Ogasawara, K. 1247
Ojeda, R. 1316
Pak, C. S. 1271
Pandey, G. 1257
Pape, A. R. 1295
Petri, A. 1181
Pini, D. 1181
Pini, E. 1265
Poplawski, J. 1304
R. Lazny et al. 1304
Radhakrishna, P. 1200
Rault, S. 1263
Reddy, B. S. N. 1251
Reddy, G. S. K. 1251
Röder, T. 1235
Rossi, E. 1265
Sakamoto, H. 1274
Salvadori, P. 1181
Sansbury, F. H. 1211
Schaller, C. 1219
Serra, S. 1241
Sharma, G. V. M. 1200
Sheppard, G. S. 1207
Shimizu, M. 1298
Siegel, K. 1227
Simpkins, N. S. 1292
Sobhana Babu, B 1261
Sochanchingwung, R. 1257
Spilling, C. D. 1295
Sreenivasulu, B. 1249
Stiebing, S. 1263
Taguchi, T. 1191
Takai, K. 1268
Takamasu, D. 1286
Tanaka, K. 1313
Tanaka, N. 1277
Tani, S. 1255
Taniguchi, T. 1247
Terao, K. 1255
Thurkauf, A. 1280
Tiwari, S. K. 1257
Utimoto, K. 1253
Vogel, P. 1219
Warren, S. 1211, 1215
Witulski, B. 1223
Yakura, T 1313
Yamamoto, H. 1283
Zhang, L. H. 1245
Zhang, W. 1319
Zhao, H. 1280
Zumbrunn, C. 1295