Chemo‐ and Regioselective Ring Construction Driven by Visible‐Light Photoredox Catalysis: an Access to Fluoroalkylated Oxazolidines Featuring an All‐Substituted Carbon Stereocenter

Abstract

Abstract The unique advantages conferred by incorporation of all‐substituted carbon stereocenters in organic molecules have gained widespread recognition. In this work, we describe a three‐component cyclization to access C ‐2 fluoroalkylated oxazolidines by fragments assembly of readily available silyl enol ether, fluoroalkyl halide, and chiral amino alcohol in a single reaction vessel, which provides an efficient strategy for expanding the pool of pharmaceutically important heterocycles featuring an all‐substituted carbon stereocenter. This process proceeds efficiently in a chemo‐, regio‐, and stereoselective fashion under mild reaction conditions at room temperature and exhibits broad functional group tolerance. The successful realization of this controlled heteroannulation sequence relies on distinctive perfluoroalkylation, regio‐ and stereoselective radical cyclization through visible‐light photoredox catalysis. Moreover, a one‐pot procedure directly employing ketone as substrate has also been achieved. magnified image