Enantioselective Synthesis of Trifluoromethyl-Substituted Cyclopropanes

Justin R. Denton, Dinesh Sukumaran and Huw M. L. Davies*

*Department of Chemistry, Emory University, Atwood Hall 440, Atlanta, GA 30322, Email: hmdavieemory.edu

J. R. Denton, D. Sukumaran, H. M. L. Davies, Org. Lett., 2007, 9, 2625-2628.

DOI: 10.1021/ol070714f

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Abstract

The reaction of 1-aryl-2,2,2-trifluorodiazoethanes with alkenes provides trifluoromethyl-substituted cyclopropanes with high diastereoselectivity and enantioselectivity in the presence of an adamantylglycine-derived dirhodium complex Rh₂(R-PTAD)₄ as catalyst.

see article for more examples

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Asymmetric Intermolecular C-H Functionalization of Benzyl Silyl Ethers Mediated by Chiral Auxiliary-Based Aryldiazoacetates and Chiral Dirhodium Catalysts

H. M. L. Davies, S. J. Hedley, B. R. Bohall, J. Org. Chem., 2005, 70, 10737-10742.

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Key Words

Cyclopropanes, Diazo Compounds, Manganese(IV) Oxide

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ID: J54-Y2007-2120