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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 S(N)2-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).

Original publication

DOI

10.1021/jo101614f

Type

Journal article

Journal

J Org Chem

Publication Date

19/11/2010

Volume

75

Pages

7745 - 7756