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?

RSC Advances Pub Date: 2017-01-17 DOI: 10.1039/C6RA27710A

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.

Graphical abstract: 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
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