A novel method of three-carbon elongation using bis(tributylstannyl)propanol

被引：14

作者：

Isono, N ^{[1
]}

Mori, M ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 51期

关键词：

D O I：

10.1016/0040-4039(95)02024-J

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of Me(3)SiSnBu(3) with methyl propiolate in DMF gave methyl 3,3-bistributylstannyl propionate 4 in a high yield. The reduction of 4 with LiAlH4 followed by treatment with MOMCl gave 3,3-bistributylstannyl propanol derivative 7d in a quantitative yield, which was a useful reagent for the C-3 unit elongation. Treatment of 7d with BuLi in THF in the presence of HMPA gave alpha-stannylated carbanion 10, which reacted with various electrophiles, such as carbonyl carbons of aldehyde, ketone, and ester, to give C-3 elongation products.

引用

页码：9345 / 9348

页数：4

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