One-pot conversions of olefins to cyclic carbonates and secondary allylic and homoallylic amines to cyclic carbamates.
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).
Davies
Stephen G
SG
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K.
Fletcher
Ai M
AM
Kurosawa
Wataru
W
Lee
James A
JA
Poce
Giovanna
G
Roberts
Paul M
PM
Thomson
James E
JE
Williamson
David M
DM