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Synlett 2011(5): 699-701  
DOI: 10.1055/s-0030-1259561
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Oxazolidinone and Tosyl Enamines by Tertiary Amine Catalysis

Nicholas A. Eddy, Peter D. Morse, Martha D. Morton, Gabriel Fenteany*
Department of Chemistry, University of Connecticut, Storrs, CT 06269, USA
Fax: +1(860)4862981; e-Mail: gabriel.fenteany@uconn.edu;
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Publikationsverlauf

Received 24 November 2010
Publikationsdatum:
22. Februar 2011 (online)

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Abstract

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.

Key words

enamine - oxazolidinone - tosyl imide - catalysis

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12

Compound 2 appeared as a single band from chromatog-raphic techniques; additionally, compound 2 underwent palladium hydrogenation, and its spectra were in accordance with the reduced enamine (see Supporting Information).

14

The freed allenone yielded a black tar, possibly the result of decomposition or polymerization.

15

For experimental procedures and compound characteri-zation data, see Supporting Information.