REACTION OF LITHIUM DIPHENYLPHOSPHONIUM DI(METHYLIDE) WITH CARBONIC-ACID DERIVATIVES - A NOVEL ACCESS TO POLYFUNCTIONAL UNSATURATED ESTERS AND AMIDES

被引：6

作者：

CRISTAU, HJ

PERRAUDDARCY, A

RIBEILL, Y

机构：

[1] Laboratoire de Chimie Organique, E.N.S.C.M, Montpellier, 34053, URA 458 (associée au C.N.R.S.)

来源：

HETEROATOM CHEMISTRY | 1992年 / 3卷 / 04期

关键词：

D O I：

10.1002/hc.520030416

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The lithium diphenylphosphonium di(methylide) Ph2P(CH2)2Li 1 readily attacks cyclic carbonates, carbamates, and thiocarbamates, resulting in "pseudo-acylation" products, after a ring-opening step. Thus, new stabilized ylides are prepared, which can be used in situ as carbonyl olefination reagents towards aldehydes. This procedure is a new one-pot method for the synthesis of (E)-vinylic esters and amides, bearing a free omega-hydroxyl group. When a thiocarbamate is the initial substrate for 1, a Michael-type cyclization occurs, following the Wittig olefination, resulting in the one-pot preparation of 7-membered heterocycles.

引用

页码：415 / 422

页数：8

共 26 条

[1]

BAYSSAT M, 1973, CHIM THER, V8, P202

[2]

BOUDIA DB, 1989, TETRAHEDRON LETT, V30, P5263

[3] ACTIVATION OF METHYLENETRIPHENYLPHOSPHORANE BY REACTION WITH TERT-BUTYLLITHIUM OR SEC-BUTYLLITHIUM [J].