4.8 Article

Enamine-Iminium Ion Nazarov Cyclization of α-Ketolenones

Journal

ORGANIC LETTERS
Volume 12, Issue 3, Pages 440-443

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol9025765

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Funding

  1. National Institutes of Health [GM57873]

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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.

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