Practical Stereoselective Synthesis of an α-Trifluoromethyl-α-alkyl Epoxide via a Diastereoselective Trifluoromethylation Reaction
The Journal of Organic Chemistry2006Vol. 72(1), pp. 292–294
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Jinhua J. Song, Zhulin Tan, Jinghua Xu, Jonathan T. Reeves, Nathan K. Yee, Ranjit Ramdas, Fabrice Gallou, Katie Kuzmich, Lisa DeLattre, Heewon Lee, XuWu Feng, Chris H. Senanayake
Abstract
A practical stereoselective synthesis is reported for an alpha-trifluoromethyl-alpha-alkyl epoxide (1), which is an important pharmaceutical intermediate. The key step involves a chiral auxiliary-controlled asymmetric trifluoromethylation reaction for the introduction of the unique trifluoromethyl-substituted tertiary alcohol stereogenic center in the target molecule. The fluoride-initiated CF3 addition to chiral keto ester 6a proceeded with a diastereoselectivity up to 86:14. The major diastereomer was readily obtained with a >99.5:0.5 dr through a simple crystallization of the crude product mixture.
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