Tetrahedron

Silicon in synthesis—17: Chloromethyl (trimethylsilyl) lithium—anew reagent for the direct conversion of aldehydes and ketones into⇌, β,-epoxytrimethylsilanes

C Burford, F Cooke, G Roy, P Magnus

Index: Burford, Clifford; Cooke, Frank; Roy, Glenn; Magnus, Philip Tetrahedron, 1983 , vol. 39, # 6 p. 867 - 876

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Citation Number: 57

Abstract

Treatment of chloromethyltrimethylsilane 1 with sec-BuLi in THF at-78° produces chloromethyl (tri-methylsilyl) lithium 4. Treatment of 4 with a wide range of aldehydes and ketones gives⇌, β-epoxytrimethylsilanes 5–28, which on acidic hydrolysis give homologated aldehydes.

~87%

~79%

~83%

~75%

~80%

~82%

~71%

~86%

~94%

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