Construction of Chiral β-Trifluoromethyl Alcohols Enabled by Catalytic Enantioselective Aldol-Type Reaction of CFCHN.

Org Lett

Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Center of Chemical Science & Engineering , Tianjin University, Tianjin 300072 , P. R. of China.

Published: June 2019

A zinc-/quinine-mediated enantioselective Aldol-type reaction of trifluorodiazoethane (CFCHN) with various aldehydes is described. This study demonstrated the feasibility of utilizing CFCHN as an effective hard nucleophile in catalytic asymmetric transformations. Furthermore, the synthetic utility of this protocol is exemplified by the construction of a diverse set of chiral β-trifluoromethylated alcohols, including a valuable HDAC inhibitor precursor.

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http://dx.doi.org/10.1021/acs.orglett.9b01468DOI Listing

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