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One-Pot Conversions of Olefins to Cyclic Carbonates and Secondary Allylic and Homoallylic Amines to Cyclic Carbamates

Stephen G. Davies, Ai M. Fletcher, Wataru Kurosawa, James A. Lee, Giovanna Poce, Paul M. Roberts, James E. Thomson and David M. Williamson

*Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K., Email: steve.davieschem.ox.ac.uk

S. G. Davies, A. M. Fletcher, W. Kurosawa, J. A. Lee, G. Poce, P. M. Roberts, J. E. Thomson, D. M. Williamson, J. Org. Chem., 2010, 75, 7745-7756.

DOI: 10.1021/jo101614f (free Supporting Information)



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Abstract

Sequential treatment of a 1,2-disubstituted olefin with m-CPBA, Br3CCO2H, and DBU results in the one-pot, stereospecific conversion of the olefin to the corresponding disubstituted cyclic carbonate. When a solution of a secondary allylic or homoallylic amine and Br3CCO2H is sequentially treated with m-CPBA then DBU, the product of the reaction is a cyclic carbamate.

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Key Words

1,3-dioxolan-2-ones, MCPBA


ID: J42-Y2010-3150