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

Xue-Qiang Chu,^aDanhua Ge,^aMao-Lin Wang,^aWeidong Rao,^bTeck-Peng Loh,^a,c,* and Zhi-Liang Shen^a,*

^aInstitute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing 211816, China

^bJiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College ofChemical Engineering, Nanjing Forestry University, Nanjing 210037, China

^cDivision of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore

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 relay visible-light photoredox catalysis. Moreover, a one-pot procedure directly employing ketone as substrate has also been achieved.

Advanced Synthesis & Catalysis2019, Early View, DOI:10.1002/adsc.201900585(2018年影响因子: 5.455)。

论文链接：https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201900585