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Enantioselective Synthesis of Secondary β-Trifluoromethyl Alcohols via Catalytic Asymmetric Reductive Trifluoroalkylation and Diastereoselective Reduction

Bing-Bing Wu, Jie Xu, Kang-Jie Bian, Qian Gao and Xi-Sheng Wang*

*Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China, Email: xswang77ustc.edu.cn

B.-B. Wu, J. Xu, K.-J. Bian, Q. Gao, X.-S. Wang, J. Am. Chem. Soc., 2022, 144, 6543-6550.

DOI: 10.1021/jacs.2c01422



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Abstract

A nickel-catalyzed asymmetric reductive cross-coupling trifluoroalkylation of acyl chlorides enables an enantioselective synthesis α-trifluoromethylated ketones. A one-pot reduction furnished alcohols bearing β-CF3-substituted stereogenic carbons with excellent diastereoselectivity. The reactions offer high yields/enantioselectivity, mild conditions, and good functional group compatibility.

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Key Words

α-trifluoromethyl carbonyl compounds, β-trifluoromethyl alcohols, manganese, sodium borohydride


ID: J48-Y2022