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

引用

页码：2046 / 2048

页数：3

共 19 条

[1]

ABOUJAOUDE EE, 1984, J ORGANOMET CHEM, P264

[2]

ARORA AS, 1972, METHOD ORGAN CHEM, V5, P278

[3] CERIUM CHLORIDE(III) PROMOTED NUCLEOPHILIC-ADDITION OF ORGANOLITHIUM REAGENTS TO ALPHA-DIPHENYLPHOSPHINOYL KETONES - AN EFFICIENT METHOD FOR THE SYNTHESIS OF HORNER-WITTIG INTERMEDIATES [J].