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Asymmetric cycloadditions of palladium-polarized aza-o-xylylenes.

ABSTRACT: Vinyl benzoxazinanones undergo highly enantioselective decarboxylative cycloadditions with electron-deficient olefins in the presence of palladium catalysts. Palladium induces the decarboxylation of the parent benzoxazinanones under mild conditions to produce an intermediate that can be described as a polarized aza-o-xylylene. These intermediates undergo a formal [4 + 2] cycloaddition with good Michael acceptors to produce highly substituted hydroquinolines with excellent regio-, diastereo-, and enantioselectivities.

SUBMITTER: Wang C

PROVIDER: S-EPMC2596915 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

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Asymmetric cycloadditions of palladium-polarized aza-o-xylylenes.

Wang Chao C Tunge Jon A JA

Journal of the American Chemical Society 20080606 26

Vinyl benzoxazinanones undergo highly enantioselective decarboxylative cycloadditions with electron-deficient olefins in the presence of palladium catalysts. Palladium induces the decarboxylation of the parent benzoxazinanones under mild conditions to produce an intermediate that can be described as a polarized aza-o-xylylene. These intermediates undergo a formal [4 + 2] cycloaddition with good Michael acceptors to produce highly substituted hydroquinolines with excellent regio-, diastereo-, and ...[more]

PMID: 18533718

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