Reaction of Baylis-Hillman products with Swern and Dess-Martin oxidants

被引：53

作者：

Lawrence, NJ

Crump, JP

McGown, AT

Hadfield, JA

机构：

[1] Cardiff Univ, Dept Chem, Cardiff CF10 3TB, S Glam, Wales

[2] Christie Hosp NHS Trust, Paterson Inst Canc Res, CRC Dept Drug Dev & Imaging, Manchester M20 4BX, Lancs, England

[3] Univ Manchester, Dept Chem, Manchester M60 1QD, Lancs, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 23期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(01)00587-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Baylis-Hillman adducts of aryl aldehydes and alkyl acrylates are efficiently oxidized to the corresponding alpha -methylene-beta -keto esters with the Dess-Martin periodinane. The attempted Swern oxidation of the same adducts resulted in S(N)2 ' -type substitution of the allylic hydroxyl group by chloride. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3939 / 3941

页数：3

共 44 条

[11]

Boeckman R.J., 1995, ENCY REAGENTS ORGANI, P4982

[12]

Boeckman R.K., 2000, J ORG SYN, V77, P141, DOI 10.15227/orgsyn.077.0141

[13] RING-A MODIFICATIONS OF PODOCARPIC ACID - TOWARDS THE SYNTHESIS OF QUASSINOIDS [J].