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Org Lett. 2013 Jan 4;15(1):26-9. doi: 10.1021/ol3029274. Epub 2012 Dec 13.

Gold-catalyzed sequential alkyne activation for the synthesis of 4,6-disubstituted phosphorus 2-pyrones.

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1
Department of Chemistry, Kangwon National University, Chuncheon 200-701, Republic of Korea.

Abstract

Tandem gold-catalyzed addition of alkynyl phosphonic acid monoethyl esters to terminal alkynes and cyclization were developed for the synthesis of 4,6-disubstituted phosphorus 2-pyrones in one reaction vessel based on the concept of sequential alkyne activation. Alkynyl enol phosphonates were selectively obtained through the gold-catalyzed addition reaction in the presence of a catalytic amount of triethylamine. Also, gold-catalyzed cyclization of alkynyl enol phosphonates was successful in giving a variety of 4,6-disubstituted phosphorus 2-pyrones.

PMID:
23236965
DOI:
10.1021/ol3029274
[Indexed for MEDLINE]
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