Practical stereoselective synthesis of an α-trifluoromethyl-α-alkyl epoxide via a diastereoselective trifluoromethylation reaction

…, F Gallou, K Kuzmich, L DeLattre, H Lee…

Index: Song, Jinhua J.; Tan, Zhulin; Xu, Jinghua; Reeves, Jonathan T.; Yee, Nathan K.; Ramdas, Ranjit; Gallou, Fabrice; Kuzmich, Katie; DeLattre, Lisa; Lee, Heewon; Feng, Xuwu; Senanayake, Chris H. Journal of Organic Chemistry, 2007 , vol. 72, # 1 p. 292 - 294

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Citation Number: 32

Abstract

A practical stereoselective synthesis is reported for an α-trifluoromethyl-α-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 ...