A NOVEL CHIRAL AUXILIARY FROM CHIRAL SPIRANES - CIS,CIS-(+) AND (-)-SPIRO[4.4]NONANE-1,6-DIOL AS CHIRAL MODIFIER IN LITHIUM ALUMINUM-HYDRIDE REDUCTION OF PHENYL ALKYL KETONES

被引:83
作者
SRIVASTAVA, N [1 ]
MITAL, A [1 ]
KUMAR, A [1 ]
机构
[1] CENT DRUG RES INST,DIV PROC DEV,LUCKNOW 226001,UTTAR PRADESH,INDIA
关键词
D O I
10.1039/c39920000493
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
LiAlH4 reduction of phenyl alkyl ketones employing the hitherto unexplored chiral auxiliary cis, cis-(+)- and (-)-spiro[4.4]nonane-1,6-diol as chiral modifier gives the corresponding alcohol in 85-90% e.e. (enantiomeric excess).
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页码:493 / 494
页数:2
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共 16 条
[11]   ENANTIOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CARBONYL-COMPOUNDS - CHIRALITY TRANSFER, MULTIPLICATION, AND AMPLIFICATION [J].
NOYORI, R ;
KITAMURA, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (01) :49-69
[13]   ASYMMETRIC SYNTHESIS VIA AXIALLY DISSYMMETRIC MOLECULES .1. VIRTUALLY COMPLETE ENANTIOFACE DIFFERENTIATION IN CARBONYL GROUP REDUCTION BY A COMPLEX ALUMINUM-HYDRIDE REAGENT [J].
NOYORI, R ;
TOMINO, I ;
TANIMOTO, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (11) :3129-3131
[14]   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
[15]   ASYMMETRIC SYNTHESIS VIA AXIALLY DYSSYMMETRIC MOLECULES .2. HIGHLY EFFICIENT SYNTHESIS OF PROSTAGLANDIN INTERMEDIATES POSSESSING THE 15S CONFIGURATION [J].
NOYORI, R ;
TOMINO, I ;
NISHIZAWA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (19) :5843-5844
[16]  
1982, ENCY CHEM TECHNOLOGY, V17, P311