Sequential treatment of a 1,2-disubstituted olefin with m-CPBA, Br 3CCO2H, 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 Br 3CCO2H 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). © 2010 American Chemical Society.
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; Poce, Giovanna; Paul M., Roberts; James E., Thomson; David M., Williamson. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 75:22(2010), pp. 7745-7756. [10.1021/jo101614f]
One-pot conversions of olefins to cyclic carbonates and secondary allylic and homoallylic amines to cyclic carbamates
POCE, Giovanna;
2010
Abstract
Sequential treatment of a 1,2-disubstituted olefin with m-CPBA, Br 3CCO2H, 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 Br 3CCO2H 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). © 2010 American Chemical Society.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
