Synthesis of homoallylic sulfones through a decarboxylative Claisen rearrangement reaction

被引：37

作者：

Bourgeois, D

Craig, D

King, NP

Mountford, DM

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] GlaxoSmithKline Res Ltd, Neurol & GI Ctr Excellence Drug Discovery, Harlow CM19 5AW, Essex, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 04期

基金：

中国国家自然科学基金;

关键词：

C-C coupling; Claisen rearrangement; homogeneous catalysis; microwave-assisted synthesis; synthetic methods;

D O I：

10.1002/anie.200462023

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A high-yielding preparation of homoallylic sulfones 2 entails the treatment of allylic tosylacetate esters 1 with stoichiometric or substoichiometric quantities of BSA and substoichiometric quantities of KOAc under conventional thermal or microwave conditions. A possible mechanism involves silyl ketene acetal formation, [3,3]-sigmatropic rearrangement, and desilylation- decarboxylation. BSA = N,O-bis(trimethylsilyl)acetamide; Ts = p-toluenesulfonyl.

引用

页码：618 / 621

页数：4