Asymmetric Synthesis of Quaternary β-Perfluorophenyl-β-amino-indolin-2-ones

Reported herein is a design and synthesis of N-tertbutylsulfinyl-( perfluoro) benzaldimine, and a study of its reactivity and stereocontrolling properties in Mannich addition reactions with indolinone derived tertiary enolates generated in situ. The corresponding products, quaternary beta-perfluorophen-yl-beta-amino-indolin-2-ones, were obtained with good to excellent yields and diastereoselectivity, underscoring the exciting synthetic potential of this newly introduced pentafluorophenyl-containing chiral imine.