Synthesis of Oxazolidinone and Tosyl Enamines by Tertiary Amine Catalysis

Synlett. 2011 Jan 1:5:699-701. doi: 10.1055/s-0030-1259561.


A procedure for the synthesis of oxazolidinone and tosyl enamines is reported. Alkynoyl oxazolidinones and tosyl imides undergo reaction to form enamines in the presence of catalytic amounts of tertiary amines. The data suggest that an amide anion is formed during the reaction, which undergoes conjugate addition to form the final product.