The synthesis and Diels-Alder reactions of (E)- and (Z)-1-methoxy-3-(phenylsulfinyl)buta-1,3-dienes

被引：35

作者：

Adams, H

Anderson, JC

Bell, R

Jones, DN ^{[1
]}

Peel, MR

Tomkinson, NCO

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

[2] Univ Sheffield, Dept Crystallog, Sheffield S3 7HF, S Yorkshire, England

[3] Glaxo Wellcome Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 23期

关键词：

D O I：

10.1039/a806470i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mild and efficient generation of benzenesulfenic acid by the thermolysis of ethyl 2-ethoxycarbonyl-3-(phenylsulfinyl)butanoate 8 in refluxing dichloromethane, and its in situ trapping with (E)- and (Z)-1-methoxybut-2-en-3-yne to form (E)-1-methoxy-3-(phenylsulfinyl)buta-1,3-diene 10 and (Z)-1-methoxy-3-(phenylsulfinyl)buta-1,3-dienes 11 respectively proceeds in high yield. The lithium perchlorate catalysed Diels-Alder reaction of 10 with both symmetrical and unsymmetrical carbonyl activated dienophiles proceeds with complete regioselectivity and in some cases complete endo-selectivity.

引用

页码：3967 / 3973

页数：7

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