BINAP/AgOTf/KF/18-crown-6 as new bifunctional catalysts for asymmetric Sakurai-Hosomi allylation and Mukaiyama aldol reaction

M Wadamoto, N Ozasa, A Yanagisawa…

Index: Wadamoto, Manabu; Ozasa, Nobuko; Yanagisawa, Akira; Yamamoto, Hisashi Journal of Organic Chemistry, 2003 , vol. 68, # 14 p. 5593 - 5601

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Citation Number: 110

Abstract

A catalytic amount of KF⊙ 18-crown-6 complex is effective as a soluble fluoride source to activate an asymmetric Sakurai-Hosomi allylation with BINAP and silver (I) triflate catalyst. The allylation of a variety of aromatic, α, β-unsaturated and aliphatic aldehydes with allylic trimethoxysilane resulted in high yields and remarkable enantioselectivities. In addition, the asymmetric Mukaiyama-type aldol reaction is achieved by using trimethoxysilyl enol ...