Desymmetrization of 4-dimethylsiloxy-1,6-heptadiynes through sequential double silylformylation

被引：14

作者：

Bonafoux, D ^{[1
]}

Ojima, I ^{[1
]}

机构：

[1] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 09期

关键词：

D O I：

10.1021/ol0156594

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Desymmetrization of dimethylsilyloxyalkadiynes (1) by Rh-catalyzed intramolecular silylformylation affords 5-exo-(formylmethylene)-oxasilacyclopentanes 2 in high yields. Novel sequential double silylformylation of 1a also provides desymmetrization, giving 3-(3-silyl-2-formylprop-2-enyl)-5-exo-(formylmethylene)oxasilacyclopentanes 4 in excellent yields. Reduction of 2a and 4 with NaBH4 gives the corresponding 5-exo-(hydroxymethylmethylene)oxasilacyclopentanes 3a and 5, respectively.

引用

页码：1303 / 1305

页数：3

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