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DOI: 10.1055/s-0030-1259561
Synthesis of Oxazolidinone and Tosyl Enamines by Tertiary Amine Catalysis
Publication History
Publication Date:
22 February 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
- Supporting Information for this article is available online:
- Supporting Information
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References and Notes
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).
14The freed allenone yielded a black tar, possibly the result of decomposition or polymerization.
15For experimental procedures and compound characteri-zation data, see Supporting Information.