Journal
ORGANIC LETTERS
Volume 14, Issue 3, Pages 874-877Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol203398e
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Funding
- National Science Foundation [CHE-0911264, OCI-0722819, CHE-0922973]
- Research Corporation for Science Advancement
- Arnold and Mabel Beckman Foundation
- Calvin College
- UC-Irvine
- Pleotint, LLC
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0922973] Funding Source: National Science Foundation
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A new Au(III)-catalyzed tandem amination-hydration reaction has been discovered, leading to the formation of alpha-(N-2-pyridonyl)ketones and heterocyclic analogues in good to excellent yields (14 examples, 48-90%). This reaction demonstrates the unusual use of a heterocyclic sp(2) nitrogen nucleophile in a gold-catalyzed 6-endo-dig cyclization. The tandem process allows rapid access to alpha-(N-2-pyridonyl)ketones, making them a convenient building block for the synthesis of more complex N-alkyl pyridone targets.
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