Construction of Chiral β-Trifluoromethyl Alcohols Enabled by Catalytic Enantioselective Aldol-Type Reaction of CF3CHN2

Meng-Yu Rong; Lijun Yang; Jing Nie; Fa-Guang Zhang; Jun-An Ma

doi:10.1021/acs.orglett.9b01468

Construction of Chiral β-Trifluoromethyl Alcohols Enabled by Catalytic Enantioselective Aldol-Type Reaction of CF₃CHN₂

Org Lett. 2019 Jun 7;21(11):4280-4283. doi: 10.1021/acs.orglett.9b01468. Epub 2019 May 24.

Authors

Meng-Yu Rong¹, Lijun Yang¹, Jing Nie¹, Fa-Guang Zhang¹, Jun-An Ma^{1

2}

Affiliations

¹ 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.
² State Key Laboratory of Elemento-Organic Chemistry , Nankai University , Tianjin 300071 , P. R. of China.

PMID: 31124694
DOI: 10.1021/acs.orglett.9b01468

Abstract

A zinc-/quinine-mediated enantioselective Aldol-type reaction of trifluorodiazoethane (CF₃CHN₂) with various aldehydes is described. This study demonstrated the feasibility of utilizing CF₃CHN₂ 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.

Publication types

Research Support, Non-U.S. Gov't