Expedient synthesis of β,β-disubstituted α-methylenepropionates

被引：15

作者：

Biswas, K

Börner, C

Gimeno, J

Goldsmith, PJ

Ramazzotti, D

So, ALK

Woodward, S

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain

[3] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

来源：

TETRAHEDRON | 2005年 / 61卷 / 06期

基金：

英国工程与自然科学研究理事会;

关键词：

Baylis-Hillman; S(N)2 '; allylic substitution; organozinc; copper;

D O I：

10.1016/j.tet.2004.12.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Baylis-Hillman alcohols are excellent sources of the allylic halides ArCH=CH(CH2X)(CO2R) (X = Br. Cl: R-1= Me, Et. Bu'). The Z double bond isomers are attained in high isomeric purity (> 14: 1. ZIE). The halides are chemo- and regiospecifically transformed into the acrylates (ArCHR2)C(=CH2)(CO2R1) on treatment with Zn(R-2)(2) (R-2 =Me. Et, CH2TMS, CH(2)SiMe(2)Ome) or PrZnBr- in the presence of catalytic amounts of copper(1) salts (0.5-20 mol%) in high yield. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1433 / 1442

页数：10

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