Palladium-catalyzed Asymmetric Trifluoromethylated Allylic Alkylation of Azlactone: Efficient Access to Unsaturated α-Quaternary Stereogenic α-Amino Acid Derivatives

Abstract

An unprecedented strategy for asymmetric trifluoromethylated allylic alkylation of azlactone with α-(trifluoromethyl)allyl acetate catalyzed by a Pd(OAc)2/(R)-BINAP has been rationally designed and developed, providing various unsaturated α-quaternary α-amino acid derivatives bearing trifluoromethyl groups, contigous quaternary and tertiary stereogenic centers in good yields with exclusive regioselectivity and excellent stereoselective control under relatively mild reaction conditions. The scale-up experiment has shown no loss of reactivity and stereoselectivity, the synthetic utility of the current strategy is testified through product transformations to obtain some important bioactivity species.