synthesis 19/2010 - Thieme Chemistry

SYNTHESIS
3217 D. C. Koester
A. Holkenbrink
D. B. Werz*
3243 C. G. Frost*
H. J. Edwards
S. D. Penrose
R. Gleave
3248 H. Grugel
T. Minuth
M. M. K. Boysen*
Journal of 2010
Synthetic Organic No. 19
Chemistry October I
Recent Advances in the Synthesis of Carbohydrate Mimetics
Exploring Rhodium-Catalysed Conjugate Addition of Chiral
Alkenylboronates Using Chiral Olefin Ligands
Ph
[Rh(ethylene) 2Cl] 2
(R,R,R)-DOLEFIN
KOH, dioxane–H2O 80 °C
Ph
OMe
BF3K
[Rh(ethylene)2Cl]2
(S,S,S)-DOLEFIN
KOH, dioxane–H2O 80 °C
MAJOR
chiral alkenylboron
donor
MAJOR
R R
OMe
O
LIGAND CONTROL
OMe
O
Me
R
O
Ph
Me
Novel Olefin–Phosphorus Hybrid and Diene Ligands Derived from
Carbohydrates
HO
HO
OH
O
OH OH
D-glucose
O
OH
OH
OH
D-arabinose
HO
TrO
R 1 O
R 1 O
O
O OEt
R1 PPh2 =
Me
AcO
AcO
Ph
O OR 1
Review
Special Topics

Special Topics
Short Papers
VI Table of Contents
3259 T. J. Barker
E. R. Jarvo*
3263 L. Wang
Z.-Q. Wang
M.-H. Xu*
G.-Q. Lin*
3268 A. V. Bogdanov*
V. F. Mironov
L. I. Musin
R. Z. Musin
3271 H. Malik
F. P. J. T. Rutjes*
B. Zwanenburg*
Diene-Ligated Iridium Complexes as Catalysts for Allylation and
Methallylation Reactions of Ketones
R 1
O
R 1 = aryl, R 2 = H, Me
R 2
(2 mol%)
[Ir(cod)Cl]2
(40 mol%)
t-BuOK
R + 1
B(pin)
(1.5 equiv)
3 (20 mol%)
B(OH)
22 °C, 3 h
THF,
OH
R 2
examples
8
yield
51–87%
Highly Enantioselective Synthesis of (Diarylmethyl)amines by Rhodium-
Catalyzed Arylation of N-Nosylimines Using a Chiral Bicyclo[3.3.0]diene
Ligand
Ar 1 N Ns
+
Ar 2 B(OH)2
[RhCl(C 2H 4) 2] 2/L*
2, toluene–H2O KHF
°C, 3–4 h
40
HN
Ns
Ar 1 Ar 2
83–99% yield
ee
98–99%
Facile Synthesis of 1,1¢-Dialkylisoindigos through Deoxygenation Reaction of
Isatins and Tris(diethylamino)phosphine
N
O
R
O
(Et2N)3P
– O=P(NEt2) 3
N
R
O
Ph
L*
R = Me, allyl, CH 2CH 2Cl, n-Pr, n-Hex
H
H
Ph
R
N
O
O
60–91%
A New Expedient Synthesis of 3-Methyl-2(5H)-furanone, the Common
Substructure in Strigolactones, and Its Proposed Biosynthesis
O
O
Grubbs catalyst
70 °C
toluene,
h 18
O
O
N
R

Table of Contents VII
3274 S. Ogawa
T. Nishimine
E. Tokunaga
N. Shibata*
3282 M. Takahashi
J.-i. Atsumi
T. Sengoku
H. Yoda*
3289 Z. Li
L. Fu
J. Wei
C. Ha
D. Pei
Q. Cai*
K. Ding*
3295 H. Ma*
S. Wu
Q. Sun
H. Li
Y. Chen
W. Zhao
B. Ma
Q. Guo
Z. Lei*
J. Yan
Expeditious Synthesis of Trifluoromethylated Heterocycles:
Noncatalytic 1,3-Dipolar Cyclization of Azomethine Imines with
(a-Trifluoromethyl)acrylates
R 1
R 2
R 3
O
–
N
N
H
+
CF3
R 4 = t-Bu, Bn
R 1
4 N R COOR 2
CH2Cl2
O
N
R 3
3 CF
COOR4 Synthesis of b-Amino-Functionalized a-exo-Methylene-g-butyrolactones via
a b-Lactam Synthon Strategy
R 2
H
N
R O 1
H
OTBS
β-lactam synthons
R 2
ring opening
1)
or
H
or
N
R O 1
H
OTBS
2) lactonization
O
O
NHR 1
R 2
O
O
β-amino-functionalized
γ-butyrolactones
A Room-Temperature, Copper-Catalyzed Cascade Process for
Diethyl 2-Aryl-3,4-dihydro-4-oxo-1,1(2H)-naphthalenedicarboxylate
O
I
Ar
CH2(CO2Et) 2
+
CuI/ligand
solvent
base,
temperature
room
O
Ar
EtOOC COOEt
NHR 1
A New Method for the Synthesis of Iminoquinones via DMP-Mediated
Oxidative Reaction
R
NH2
DMP, Bu4NBr
r.t., 2–6 h, 43–75% yields, 6 examples
H
N
O
CH2Cl2
DMP
R
CH2Cl2/H2O
r.t., 3–12 h, 47–87% yields, 9 examples
N
R
N
Br
NH 2
O
O
R 2
Papers

Papers
VIII Table of Contents
3301 D. Mondal*
S. Bera
3309 K. Koroniak
G. Haufe*
3315 F. Jahani
B. Zamenian
S. Khaksar
M. Tajbakhsh*
3319 G. Revelant
S. Hesse*
G. Kirsch
A Synthetic View of an Analogue of the Spiro-b-lactone-g-lactam Ring in
Oxazolomycins and Lajollamycin
O O
O N
Bn
H
O
O
+
N
Boc
O
N
OBn
O
OH
N
Boc
OBz
O
O
spiro-β-lactone pyrrolidine
Synthesis of Enantiopure Fluorinated Ceramides; Analogues of Natural
Sphingolipids
OH
O
12 12
OEt
OH
OH
N3 F F R HN
Pyridine 2,6-Dicarboxylic Acid as a Bifunctional Organocatalyst for
Hydrophosphonylation of Aldehydes and Ketones in Water
O
R 1 R 2
R1 alkyl, aryl
=
R2 alkyl, H =
+
MeO
P OMe
OMe
PDA =
O
H
O
PDA (10 mol%)
H2O, 50 °C, 1–4 h
N
O
O H
O
R 2
OH
R1 P O
MeO
OMe
60–95%
Synthesis of Novel N-Substituted 2-(Hetero)arylimino-1,3-thiazolidin-4-ones
R 1
R 2 NH 2
S
R 1
R1 Ph, 4-MeC6H4, 4-ClC6H4, 4-MeOC6H4
=
R2 H =
R 1 –R 2 =
R 2
S
N
S
N
C6H4(4-OMe)
O
+
4-MeOC 6H 4
22–46% 10–32%
N
S
N
O
S
R 2
R 1

Table of Contents IX
3325 D. Li
Y. Zhao
L. Ye
C. Chen
J. Zhang*
3332 F. Stazi
W. Maton
D. Castoldi
P. Westerduin
O. Curcuruto
S. Bacchi*
3339 J. T. Fletcher*
M. E. Keeney
S. E. Walz
3346 C. Villarreal
R. Martínez*
A Formal Total Synthesis of Fostriecin by a Convergent Approach
O
2
3
O
diethyl D-(+)-malate
3PO NaHO
5
9
8
6
Julia–Kocienski
olefination
diethyl D-(+)-malate
OH
11
12
OH
reaction
AD
fostriecin
13
OH
Stille coupling
Efficient Methods for the Synthesis of Arylacetonitriles
R 1
R 1
CHO N OH
F
R 1
R 2 O 2C
R 1
CN
1-Allyl- and 1-Benzyl-3-methyl-1,2,3-triazolium Salts via Tandem Click
Transformations
R1 R Br 2
+
R 1 = allyl or benzyl
NaN3
4 CuSO
Na ascorbate
2O
t-BuOH–H
24 h r.t.,
R 1
N
N
N
R 1
R 2
CN
MeI
MeCN
°C, 48 h
40
Synthesis of Novel Furo-, Thieno-, and Pyrroloazepines
X
O
NH
X = NH, O, S
lactamization
X
CO2H
oxidative
radical
alkylation
NH 2
homologation
X
CO2H
N R
N N
1
I –
+
X
R 2
CO 2H
Papers

Papers
X Table of Contents
3353 J. Carreras
A. Avenoza*
J. H. Busto*
J. M. Peregrina
3358 H. Quast*
E. Schmitt
K.-H. Ross
3363 D. Žerovnik
U. Grošelj
D. Kralj
Č. Malavašič
J. Bezenšek
G. Dahmann
K. Stare
A. Meden
B. Stanovnik
J. Svete*
3374 L. Nagarapu*
V. N. Cheemalapati
S. Karnakanti
R. Bantu
Synthesis of Enantiopure Quaternary Prolines by a Metathesis Process of
2,5-Ethenoproline Derivatives
MeO 2C
Boc
N
R
HN
R CO2H
1-Acylsemicarbazides by Ring Opening of Iminodiaziridines with Carboxylic
Acids: Novel, Expeditious Access to the Azapeptide Motif
R
OH
N
+
N N O
R
O
Synthesis of 1,5,6,7-Tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-ones as
Conformationally Constrained Pyrazole Analogues of Histamine
H 2N
H 2N
MeOOC
R 1
N
N
N
R2 O
N
COOH COOH
A method
B method
R 1
N
N
N
O
N
H
method C
N
R2 R 1 = Me, Ph, t-Bu; R 2 = benzyl, (pyridin-2-yl)methyl, (tetrahydrofuran-3-yl)methyl, i-Pr
Synthesis of Annulated Pyrroles: Condensation of Aldose Sugars,
Arylamines, and 1,3-Diones Using TBAB
OH
HO
O
OH
OH
OH
+ PhNH2 +
O
O
R
TBAB
Ac 2O, DMAP
O
AcO
O
AcO
O
R = Me, OEt
O
N
Ph
R

Table of Contents XI
3379 A. V. Chemagin
N. V. Yashin*
Y. K. Grishin
T. S. Kuznetsova
N. S. Zefirov
3384 S. Chatterjee
G. Ye
Y. Song
B. L. Barker
C. U. Pittman Jr.*
Synthesis of a-Aminocyclopropylphosphonic Acids
NO2
P(O)(OEt)2
Zn, AcOH
NH2
1. TMSBr
i-PrOH 2. propylene oxide, EtOH
P(O)(OEt)2
81−91% 82−95%
Reactions of Substituted Oxazoles and Thiazoles with Acid Chlorides:
Carbon–Carbon Bond Formation through Cyclic Ketene Acetals
N X
1) n-BuLi, THF, –78 °C
XV Forthcoming Articles
Ar
O
O
Ar
O
Ar
2) ArCOCl, –78 °C to r.t.
N X
( X = O, S)
Et3N, ArCOCl
MeCN, reflux
Ar
O
O
Ar
N X
but no
Ar
O
NH2
P(O)(OH)2
O
N X
Ar
Papers

XII Table of Contents
Author Index
Atsumi, J.-i. 3282
Avenoza, A. 3353
Bacchi, S. 3332
Bantu, R. 3374
Barker, B. L. 3384
Barker, T. J. 3259
Bera, S. 3301
Bezenšek, J. 3363
Bogdanov, A. V. 3268
Boysen, M. M. K. 3248
Busto, J. H. 3353
Cai, Q. 3289
Carreras, J. 3353
Castoldi, D. 3332
Chatterjee, S. 3384
Cheemalapati, V. N. 3374
Chemagin, A. V. 3379
Chen, C. 3325
Chen, Y. 3295
Curcuruto, O. 3332
Dahmann, G. 3363
Ding, K. 3289
Edwards, H. J. 3243
Fletcher, J. T. 3339
Frost, C. G. 3243
Fu, L. 3289
Gleave, R. 3243
Grishin, Y. K. 3379
Grošelj, U. 3363
Grugel, H. 3248
Guo, Q. 3295
Ha, C. 3289
Haufe, G. 3309
Hesse, S. 3319
Holkenbrink, A. 3217
Jahani, F. 3315
Jarvo, E. R. 3259
Karnakanti, S. 3374
Keeney, M. E. 3339
Khaksar, S. 3315
Kirsch, G. 3319
Koester, D. C. 3217
Koroniak, K. 3309
Kralj, D. 3363
Kuznetsova, T. S. 3379
Lei, Z. 3295
Li, D. 3325
Li, H. 3295
Li, Z. 3289
Lin, G.-Q. 3263
Ma, B. 3295
Ma, H. 3295
Malavašič, Č. 3363
Malik, H. 3271
Martínez, R. 3346
Maton, W. 3332
Meden, A. 3363
Minuth, T. 3248
Mironov, V. F. 3268
Mondal, D. 3301
Musin, L. I. 3268
Musin, R. Z. 3268
Nagarapu, L. 3374
Nishimine, T. 3274
Ogawa, S. 3274
Pei, D. 3289
Penrose, S. D. 3243
Peregrina, J. M. 3353
Pittman Jr., C. U. 3384
Quast, H. 3358
Revelant, G. 3319
Ross, K.-H. 3358
Rutjes, F. P. J. T. 3271
Schmitt, E. 3358
Sengoku, T. 3282
Shibata, N. 3274
Song, Y. 3384
Stanovnik, B. 3363
Stare, K. 3363
Stazi, F. 3332
Sun, Q. 3295
Svete, J. 3363
Tajbakhsh, M. 3315
Takahashi, M. 3282
Tokunaga, E. 3274
Villarreal, C. 3346
Walz, S, E. 3339
Wang, L. 3263
Wang, Z.-Q. 3263
Wei, J. 3289
Werz, D. B. 3217
Westerduin, P. 3332
Wu, S. 3295
Xu, M.-H. 3263
Yan, J. 3295
Yashin, N. V. 3379
Ye, G. 3384
Ye, L. 3325
Yoda, H. 3282
Zamenian, B. 3315
Zefirov, N. S. 3379
Žerovnik, D. 3363
Zhang. J. 3325
Zhao, W. 3295
Zhao, Y. 3325
Zwanenburg, B. 3271