Asymmetric synthesis of γ-hydroxy α,β-unsaturated aldehydes via enantioselective direct addition of propargyl acetate to aldehydes

被引：118

作者：

El-Sayed, E ^{[1
]}

Anand, NK ^{[1
]}

Carreira, EM ^{[1
]}

机构：

[1] ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 19期

关键词：

D O I：

10.1021/ol016431j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] We report the first example of enantioselective and diastereoselective aldehyde additions of propargyl acetate to aldehydes using the methodology recently reported from our laboratories. Subsequent O-silyl protection, Pd-catalyzed isomerization, AcOH addition, and hydrolysis result in optically active gamma -hydroxy alpha,beta -unsaturated aldehydes as powerful building blocks.

引用

页码：3017 / 3020

页数：4

共 38 条

[1] ARAI M, 1992, SYNLETT, P309
[2] Synthetic studies towards oxylipins: total synthesis of Constanolactones A and B
Barloy-Da Silva, C
Benkouider, A
Pale, P
[J]. TETRAHEDRON LETTERS, 2000, 41 (17) : 3077 - 3081
[3] ASYMMETRIC-SYNTHESIS OF GAMMA-HYDROXY ALPHA,BETA-UNSATURATED AMIDES VIA AN AD-ELIMINATION PROCESS - SYNTHESIS OF (+)-CORIOLIC ACID
BENNANI, YL
SHARPLESS, KB
[J]. TETRAHEDRON LETTERS, 1993, 34 (13) : 2083 - 2086
[4] Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes
Boyall, D
López, F
Sasaki, H
Frantz, D
Carreira, EM
[J]. ORGANIC LETTERS, 2000, 2 (26) : 4233 - 4236
[5] OPTICALLY-ACTIVE BUILDING-BLOCKS FROM THE SPAC REACTION - A COMPLETELY ASYMMETRIC-SYNTHESIS OF (4S-CIS)-5-(CYCLOHEXYLMETHYL)-4-HYDROXY-2-PYRROLIDINONE, A STATINE ANALOG
BURGESS, K
CASSIDY, J
HENDERSON, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) : 2050 - 2058
[6] INTRAMOLECULAR DIELS-ALDER REACTIONS OF SILYL ACETAL TRIENES - THE EFFECT ON STEREOSELECTIVITY OF ALLYLIC SUBSTITUTION
CRAIG, D
READER, JC
[J]. TETRAHEDRON LETTERS, 1992, 33 (28) : 4073 - 4076
[7] Drager G, 1998, CHEM-EUR J, V4, P1324
[8] C-2-symmetric copper(II) complexes as chiral Lewis acids. Catalytic enantioselective aldol additions of silylketene acetals to (benzyloxy)acetaldehyde
Evans, DA
Murry, JA
Kozlowski, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (24) : 5814 - 5815
[9] Enantiodivergent total syntheses of (+)- and (-)-scopadulcic acid A
Fox, ME
Li, C
Marino, JP
Overman, LE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (23) : 5467 - 5480
[10] Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes
Frantz, DE
Fässler, R
Carreira, EM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) : 1806 - 1807

← 1 2 3 4 →