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Gold-catalyzed [3+3]-annulation of azomethine imines with propargyl esters.

ABSTRACT: The gold-catalyzed [3+3]-cycloaddition reaction of propargyl esters and azomethine imines has been developed. The reaction provides a rapid entry into a wide range of substituted tetrahydropyridazine derivatives from simple starting materials. A stepwise mechanism involving addition of the 1,3-dipole to a gold-carbenoid intermediate is proposed.

SUBMITTER: Shapiro ND

PROVIDER: S-EPMC2763378 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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Gold-catalyzed [3+3]-annulation of azomethine imines with propargyl esters.

Shapiro Nathan D ND Shi Yun Y Toste F Dean FD

Journal of the American Chemical Society 20090801 33

The gold-catalyzed [3+3]-cycloaddition reaction of propargyl esters and azomethine imines has been developed. The reaction provides a rapid entry into a wide range of substituted tetrahydropyridazine derivatives from simple starting materials. A stepwise mechanism involving addition of the 1,3-dipole to a gold-carbenoid intermediate is proposed. ...[more]

PMID: 19645449

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