Allyldimethylsilyl triflate: a self-catalyzed silyl nucleophile

Abstract

Allyldimethylsilyl triflate 2 may be prepared by a protiodesilylation reaction between diallyldimethylsilane and triflic acid. This compound possesses both a silyl-substituted carbon nucleophile and the Lewis acid necessary for activation of an electrophile. Upon exposure to an aromatic aldehyde (e.g., p-MeOC6H4CHO), the homoallylic alcohol 4 is formed in good yield. The synthetic advantages of the intramolecular Cope-type cyclization reaction are discussed.