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

Huw M. L. Davies,* Simon J. Hedley and Brooks R. Bohall

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

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

DOI: 10.1021/jo051747g

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C-H functionalization of benzyl silyl ethers by means of rhodium-catalyzed insertions of aryldiazoacetates can be achieved in a highly diastereoselective and enantioselective manner by judicious choice of chiral catalyst or auxiliary. The use of (S)-lactate as a chiral auxiliary resulted in C-H functionalization with moderate diastereoselectivity and enantioselectivity. The best results were achieved using Hashimoto's Rh2((S)-PTTL)4 catalyst.

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Enantioselective Synthesis of Trifluoromethyl-Substituted Cyclopropanes

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

Key Words

1,3-diols, β-hydroxy esters, α-Diazo Ester

ID: J48-Y2005-2110