CsF-Catalyzed Nucleophilic Trifluoromethylation of trans-Enones with Trimethyl(trifluoromethyl)silane:  A Facile Synthesis of trans-α-Trifluoromethyl Allylic Alcohols

Rajendra P. Singh, Robert L. Kirchmeier and Jean'ne M. Shreeve

*Department of Chemistry, University of Idaho, Moscow, Idaho 83844-2343, Email: jshreeveuidaho.edu

R. P. Singh, R. L. Kirchmeier, J. M. Shreeve, Org. Lett., 1999, 1, 1047-1049.

DOI: 10.1021/ol990781c

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Abstract

Reactions of enones with TMSCF₃ in the presence of catalytic amounts of CsF in ethylene glycol dimethyl ether provide α-trifluoromethyl silyl ethers in essentially quantitative yield. On hydrolysis with aqueous HCl, the corresponding trans-α-trifluoromethyl allylic alcohols were formed in >90% isolated yield.

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Key Words

trifluoromethylation

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ID: J54-Y1999