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: hmdavie
emory.edu
H. M. L. Davies, S. J. Hedley, B. R. Bohall, J. Org. Chem., 2005, 70, 10737-10742.
DOI: 10.1021/jo051747g
see article for more examples
Abstract
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.
see article for more examples
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
