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
收藏
页码：3967 / 3973
页数：7
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