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Cyclization reactions through DDQ-mediated vinyl oxazolidinone oxidation.

ABSTRACT: Vinyl oxazolidinones react with DDQ to form alpha,beta-unsaturated acyliminium ions in a new method for forming electrophiles under oxidative conditions. Appended nucleophiles undergo 1,4-addition reactions with these intermediates to form cyclic vinyl oxazolidinones with good levels of diastereocontrol, highlighting a new approach to utilizing oxidative carbon-hydrogen bond functionalization to increase molecular complexity.

SUBMITTER: Liu L

PROVIDER: S-EPMC2722373 | biostudies-literature | 2009 Jul

REPOSITORIES: biostudies-literature

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Cyclization reactions through DDQ-mediated vinyl oxazolidinone oxidation.

Liu Lei L Floreancig Paul E PE

Organic letters 20090701 14

Vinyl oxazolidinones react with DDQ to form alpha,beta-unsaturated acyliminium ions in a new method for forming electrophiles under oxidative conditions. Appended nucleophiles undergo 1,4-addition reactions with these intermediates to form cyclic vinyl oxazolidinones with good levels of diastereocontrol, highlighting a new approach to utilizing oxidative carbon-hydrogen bond functionalization to increase molecular complexity. ...[more]

PMID: 19552390

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