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Gold-Catalyzed 1,3-Transposition of Ynones

Author:
Kazem Shiroodi, Roohollah, Soltani, Mohammad, Gevorgyan, Vladimir
Source:
Journal of the American Chemical Society 2014 v.136 no.28 pp. 9882-9885
ISSN:
1520-5126
Subject:
chemical bonding, electronics, gold, stereochemistry, thermodynamics
Abstract:
An efficient, regioselective gold-catalyzed 1,3-transposition reaction of ynones and diynones has been developed. It was found that stereoelectronic (interrupted conjugation) and electronic (extended conjugation) factors could efficiently govern the regioselectivity of this thermodynamically controlled transformation. The produced conjugated diynones were efficiently transformed into diverse alkyne-substituted five- and six-membered heterocycles.
Agid:
5391895