Tetrahedron

Organotin and-mercury routes to enones, dienones amd spiroacetals

MG O'Shea, W Kitching

Index: O'Shea, Michael G.; Kitching, William Tetrahedron, 1989 , vol. 45, # 4 p. 1177 - 1186

Full Text: HTML

Citation Number: 20

Abstract

Conjugate addition of trinethyltinlithium to cyclohex-2-enone followed by enolate trapping with alkylating agents provide traus-2-alkyl-3-trimethylstannylcyclohexanones, which on reaction with Grignard reagents derived from 4-bromo-1-butene or 5-bromo-1-pentene afford tertiary γ-stannylcyclohexanols in a highly diastereoselective fashion. Triaethylstannyl- triggered ring fragmentation (by lead tetraacetate in benzene) leads efficiently to dienones ...