GENERATION OF ENANTIOMERICALLY ENRICHED LITHIUM INDENIDES BY MEANS OF (-)-SPARTEINE - STRUCTURE, STEREOSELECTIVE SUBSTITUTION, AND SOLVENT EFFECTS

被引:102
作者
HOPPE, I
MARSCH, M
HARMS, K
BOCHE, G
HOPPE, D
机构
[1] UNIV MARBURG,FACHBEREICH CHEM,D-35032 MARBURG,GERMANY
[2] UNIV MUNSTER,INST ORGAN CHEM,D-48149 MUNSTER,GERMANY
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 19期
关键词
ASYMMETRIC SYNTHESES; CHIRAL AUXILIARIES; INDENES; LITHIUM COMPOUNDS;
D O I
10.1002/anie.199521581
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The thermodynamically controlled equilibration of the configurationally labile diastereomeric lithium 1‐alkylindenide/(–)‐sparteine complexes in diethyl ether/hexane combined with the crystallization of the diastereomer shown (1; R = Me, nBu) results in a stereoselective addition of these complexes to carbonyl compounds with enantiofacial differentiation at the indenide moiety. In THF/hexane, however, the solvent displaces the chiral ligand and leads to complete racemization of the products. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
引用
收藏
页码:2158 / 2160
页数:3
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