Enantioselective reduction of esters:: synthesis of optically active α-acetoxy ethers

被引:9
作者
Rychnovsky, SD [1 ]
Bax, BM [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
关键词
D O I
10.1016/S0040-4039(00)00470-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective reduction and acetylation of esters to alpha-acetoxy ethers is described. Reduction with a NaAlH4-ephedrine reagent followed by in situ acetylation gives 2 with good enantiomeric excess. This reaction is limited in scope, but it demonstrates that enantioselective reductions of esters are possible. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3593 / 3596
页数:4
相关论文
共 13 条
[1]   CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS [J].
ALEXAKIS, A ;
MANGENEY, P .
TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :477-511
[2]  
CHA JS, 1995, ORG PREP P INT, V27, P94
[3]   General synthesis of alpha-acetoxy ethers from esters by DIBALH reduction and acetylation [J].
Dahanukar, VH ;
Rychnovsky, SD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8317-8320
[4]   ALKYLMETAL ASYMMETRIC REDUCTION .9. ASYMMETRIC REDUCTION OF ALKYL PHENYL KETONES BY STERICALLY HINDERED CHIRAL ORGANOALUMINUM COMPOUNDS [J].
GIACOMELLI, G ;
MENICAGLI, R ;
CAPORUSSO, AM ;
LARDICCI, L .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (09) :1790-1793
[5]   ALKYLMETAL ASYMMETRIC REDUCTION .13. A STERICALLY CROWDED CHIRAL ORGANO-ALUMINUM COMPOUND AS A REDUCING AGENT OF KETONES [J].
GIACOMELLI, G ;
LARDICCI, L ;
PALLA, F .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (02) :310-313
[6]  
KANAZAWA R, 1976, SYNTHESIS-STUTTGART, P526
[7]   Synthesis and Lewis acid-catalyzed nucleophilic substitution of chiral 1-alkoxyalkyl carboxylates [J].
Matsutani, H ;
Ichikawa, S ;
Yaruva, J ;
Kusumoto, T ;
Hiyama, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (19) :4541-4542
[8]  
NAGASHIMA N, 1991, CHEM PHARM BULL, V39, P1972
[9]   ASYMMETRIC-SYNTHESIS VIA AXIALLY DISSYMMETRIC MOLECULES .6. RATIONAL DESIGNING OF EFFICIENT CHIRAL REDUCING AGENTS - HIGHLY ENANTIOSELECTIVE REDUCTION OF AROMATIC KETONES BY BINAPHTHOL-MODIFIED LITHIUM ALUMINUM-HYDRIDE REAGENTS [J].
NOYORI, R ;
TOMINO, I ;
TANIMOTO, Y ;
NISHIZAWA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (22) :6709-6716
[10]  
SCHMID CR, 1993, ORG SYNTH, V72, P6