The Journal of Organic Chemistry

Novel Method of Three-Carbon Elongation Using Bis (tributylstannyl) propanol

N Isono, M Mori

Index: Isono, Naohiro; Mori, Miwako Journal of Organic Chemistry, 1998 , vol. 63, # 6 p. 1773 - 1779

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Citation Number: 4

Abstract

The reaction of Me3SiSnBu3 (1) with methyl propiolate in DMF in the presence of BnEt3NCl gave methyl 3, 3-bis (tributylstannyl) propionate (7) in high yield. Reduction of 7 with LiAlH4 followed by treatment with MOMCl gave 3, 3-bis (tributylstannyl) propanol derivative 17d in a quantitative yield, which was a useful reagent for C-3 unit elongation. Treatment of 17d with BuLi in THF in the presence of HMPA gave α-stannylated carbanion II, which reacted with ...