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Photocatalytic [2 + 2] Cycloadditions of Enones with Cleavable Redox Auxiliaries

Authors :
Elizabeth L. Tyson
Elliot P. Farney
Tehshik P. Yoon
Source :
Organic Letters. 14:1110-1113
Publication Year :
2012
Publisher :
American Chemical Society (ACS), 2012.

Abstract

α,β-Unsaturated 2-imidazolyl ketones undergo [2 + 2] cycloaddition with a variety of Michael acceptors upon irradiation with visible light in the presence of Ru(bpy)(3)(2+). Cleavage of the imidazolyl auxiliary from the cycloadducts affords cyclobutane carboxamides, esters, thioesters, and acids that would not be accessible from direct cycloaddition of the corresponding unsaturated carbonyl compounds.

Details

ISSN :
15237052 and 15237060
Volume :
14
Database :
OpenAIRE
Journal :
Organic Letters
Accession number :
edsair.doi.dedup.....1b57a5c2834dc487d9854bfef3338de9
Full Text :
https://doi.org/10.1021/ol3000298