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

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journal contribution
posted on 19.11.2010, 00:00 by Stephen G. Davies, Ai M. Fletcher, Wataru Kurosawa, James A. Lee, Giovanna Poce, Paul M. Roberts, James E. Thomson, David M. Williamson
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 (1,3-dioxolan-2-one). The reaction proceeds via an initial epoxidation followed by SN2-type epoxide ring opening by Br3CCO2H and subsequent base-promoted carbonate formation upon elimination of bromoform. 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 (1,3-oxazolidin-2-one or 1,3-oxazinan-2-one).