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Enamine-iminium ion Nazarov cyclization of alpha-ketoenones.

ABSTRACT: The mono-triflate salts of some chiral nonracemic 1,2-diamines react with alpha-ketoenones in a stoichiometric reaction to form products of the Nazarov cyclization in high enantiomeric ratios. The mechanism appears to involve rearrangement of an enamine-iminium ion.

SUBMITTER: Bow WF

PROVIDER: S-EPMC2854558 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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Enamine-iminium ion Nazarov cyclization of alpha-ketoenones.

Bow William F WF Basak Ashok K AK Jolit Anais A Vicic David A DA Tius Marcus A MA

Organic letters 20100201 3

The mono-triflate salts of some chiral nonracemic 1,2-diamines react with alpha-ketoenones in a stoichiometric reaction to form products of the Nazarov cyclization in high enantiomeric ratios. The mechanism appears to involve rearrangement of an enamine-iminium ion. ...[more]

PMID: 20030316

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