Asymmetric synthesis of C-F quaternary α-fluoro-β-amino-indolin-2-ones: Via Mannich addition reactions; Facets of reactivity, structural generality and stereochemical outcome

Abstract

Reported herein is a new approach for the preparation of enantiomerically pure α-fluoro-β-amino-indolin-2-ones possessing tetrasubstituted fluorinated stereogenic centers. This method includes the detrifluoroacetylative in situ generation of tertiary enolates followed by Mannich reaction with (Ss)-sulfinylimines. The operationally convenient conditions coupled with perfect diastereoselectivity and functional substituent compatibility bode well for widespread application of this new synthetic method.