CERIUM(III) CHLORIDE PROMOTED NUCLEOPHILIC-ADDITION OF ORGANOLITHIUM REAGENTS TO ALPHA-ALKYL-BETA-KETOPHOSPHINE OXIDES - A NEW PROTOCOL FOR THE SYNTHESIS OF STEREOCHEMICALLY DEFINED TRISUBSTITUTED OLEFINS

被引:39
作者
BARTOLI, G [1 ]
MARCANTONI, E [1 ]
SAMBRI, L [1 ]
TAMBURINI, M [1 ]
机构
[1] UNIV CAMERINO,I-62032 CAMERINO,ITALY
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 18期
关键词
ALKENES; ALKYLATIONS; ASYMMETRIC SYNTHESES; CERIUM COMPOUNDS; HORNER-WITTIG REACTIONS;
D O I
10.1002/anie.199520461
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Horner key intermediates 2 for the synthesis of trisbustituted stereochemically defined olefins 3 can be obtained easily be stereoselective alkylation of α‐alkyl‐β‐ketophosphine oxides 1 with RLi·CeCl3 complexes in THF at −78°C. Decomposition with KH gives trisubstituted alkenes with excellent diastereoselectivity. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
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页码:2046 / 2048
页数:3
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