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Synfacts 2011(1): 0071-0071  
DOI: 10.1055/s-0030-1259107
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Indium-Catalyzed Enantioselective Carbonyl-Ene Reaction of Trifluoropyruvate

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
J.-F. Zhao, B.-H. Tan, M.-K. Zhu, T.-B. W. Tjan, T.-P. Loh*
Nanyang Technological University, Singapore
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Publication History

Publication Date:
21 December 2010 (online)

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Significance

Asymmetric ketone-ene reaction involving trifluoropyruvate allows the preparation of enantiomerically enriched tertiary homoallylic ­alcohols containing a CF3 group, which are important building blocks for agrochemicals and pharmaceuticals. This methodology received rather limited attention despite the extensive studies of asymmetric aldehyde-ene reactions. In this paper, a highly enantioselective protocol involving the use of indium(III)-pybox catalyst in an ionic liquid is ­reported; a range of products were obtained in 74-98% yields and with up to 98% ee.