Au(III)-catalyzed tandem amination-hydration of alkynes: synthesis of α-(N-2-pyridonyl)ketones

Nathan A Romero; Benjamin M Klepser; Carolyn E Anderson

doi:10.1021/ol203398e

Au(III)-catalyzed tandem amination-hydration of alkynes: synthesis of α-(N-2-pyridonyl)ketones

Org Lett. 2012 Feb 3;14(3):874-7. doi: 10.1021/ol203398e. Epub 2012 Jan 11.

Authors

Nathan A Romero¹, Benjamin M Klepser, Carolyn E Anderson

Affiliation

¹ Department of Chemistry and Biochemistry, Calvin College, Grand Rapids, Michigan 49546, USA.

PMID: 22235809
DOI: 10.1021/ol203398e

Abstract

A new Au(III)-catalyzed tandem amination-hydration reaction has been discovered, leading to the formation of α-(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 α-(N-2-pyridonyl)ketones, making them a convenient building block for the synthesis of more complex N-alkyl pyridone targets.