The Journal of Organic Chemistry

Scope and mechanism of stannylalumination of 1-alkynes

S Sharma, AC Oehlschlager

Index: Sharma, Sunaina; Oehlschlager, Allan C. Journal of Organic Chemistry, 1989 , vol. 54, # 21 p. 5064 - 5073

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Citation Number: 71

Abstract

Terminal acetylenes react with Bu, SnAlEh in the presence of Cu+ or PdO catalysts to give 1, 2-dimetallo-l-alkenes in highly regio-and stereoselective reactions. These intermediates can be selectively functionalized at the vinyl-aluminum bond to provide vinylstannanes, which upon transmetalation and further reaction with electrophiles give stereodefined trisubstituted olefins. In sharp contrast to the normal behavior of alkylaluminum reagents, this process ...

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