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

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. (Figure presented.).