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Synthesis of Oxazolidinone and Tosyl Enamines by Tertiary Amine Catalysis.

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.

SUBMITTER: Eddy NA 

PROVIDER: S-EPMC3059314 | biostudies-literature | 2011 Jan

REPOSITORIES: biostudies-literature

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Synthesis of Oxazolidinone and Tosyl Enamines by Tertiary Amine Catalysis.

Eddy Nicholas A NA   Morse Peter D PD   Morton Martha D MD   Fenteany Gabriel G   Fenteany Gabriel G  

Synlett : accounts and rapid communications in synthetic organic chemistry 20110101

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. ...[more]

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