HIGHLY STEREOSELECTIVE ALLYLATION OF BENZALDEHYDE - GENERATION OF A STEREOCHEMICALLY DEFINED ALLYLZINC SPECIES FROM A PI-ALLYLPALLADIUM INTERMEDIATE AND DIETHYLZINC

被引：73

作者：

TAMARU, Y

TANAKA, A

YASUI, K

GOTO, S

TANAKA, S

机构：

[1] Department of Applied Chemistry, Faculty of Engineering Nagasaki University, Nagasaki, 852

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 07期

关键词：

ALLYLATION; PI-ALLYLPALLADIUM COMPOUNDS; UMPOLUNG; ZINC COMPOUNDS;

D O I：

10.1002/anie.199507871

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Umpolung of the π‐allyl group in π‐allylpalladium intermediates is possible by alkylallyl exchange with diethylzinc. The resulting nucleophilic allylzinc species can attack benzaldehyde. Thus reaction of the cyclohexenyl ester trans‐1 yields cis‐syn‐2 selectively. This stereoselectivity can be explained with transition state structure I. 1,3‐Disubstituted allyl compounds undergo analogous reactions with regio‐ and stereoselectivity. LPPh3. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany

引用

页码：787 / 789

页数：3

共 16 条

[1] REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF 1,3-HYDROXYL AMINES VIA PALLADIUM-CATALYZED CARBONATE CARBAMATE TRANSFORMATION WITH UNIQUE STEREOSELECTIVITY - SYNTHESIS OF 3-AMINO-4-PENTEN-1-OLS [J].