New carbon-carbon bond formation through oxyallylation of enoxysilanes with sulfur dioxide adduct of 1-methoxybutadiene. Stereoselective synthesis of (Z)-4-methoxy-6-oxoalk-2-enyl methyl sulfones.

被引：35
作者：
Deguin, B [1 ]
Roulet, JM [1 ]
Vogel, P [1 ]
机构：
[1] UNIV LAUSANNE,CHIM SECT,BCH,CH-1015 LAUSANNE,SWITZERLAND
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 35期
关键词：
D O I：
10.1016/S0040-4039(97)01397-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Mixtures of 1-methoxybutadiene, trimethylsilyl enol ethers, SO2 and a Lewis acid catalyst generate trimethylsilyl (Z)-4-methoxy-6-oxoalk-2-enesulfinates that can be converted into 4-methoxy-6-oxoalk-2-enyl methyl sulfones and 5-alkyl-4-methoxy-6-oxoalk-2-enyl methyl sulfones with 100% (Z) selectivity and good syn diastereoselectivity for the 5-alkyl and 4-methoxy substituents. (C) 1997 Elsevier Science Ltd.
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收藏
页码：6197 / 6200
页数：4
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