NEW CHIRAL AUXILIARIES FOR ENOLATE ALKYLATIONS

被引：28

作者：

JEONG, KS

PARRIS, K

BALLESTER, P

REBEK, J

机构：

[1] UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260

[2] MIT,DEPT CHEM,CAMBRIDGE,MA 02139

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1990年 / 29卷 / 05期

关键词：

D O I：

10.1002/anie.199005551

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereospecific synthesis (>99:1) of α‐alkylcarboxylic acids 3 has been achieved using chiral auxiliaries such as 1, which is a derivative of the Kemp triacid. Compound 1 is coupled at the imide group with the acid chloride 2. Lithiation (→enolate), alkylation, and cleavage leads to 3. The effectiveness of 1 is a consequence of the fact that it shields one side of the enolate from attack by the electrophile EX (examples: R  Me, E  PhCH2, or R  PhCH2, E  Me). (Figure Presented.) Copyright © 1990 by VCH Verlagsgesellschaft mbH, Germany

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页码：555 / 556

页数：2

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