Rauhut-Currier type homo- and heterocouplings involving nitroalkenes and nitrodienes

Reaction of nitroalkenes or nitrodienes with methyl vinyl ketone (MVK) or acrylate in the presence of the imidazole-LiCl catalyst system provides Rauhut-Currier (vinylogous Morita-Baylis-Hillman) adducts in moderate yield. Under similar conditions (imidazole-hydroquinone), nitroalkenes and nitrodien...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2010-11, Vol.8 (21), p.4867-4873
Main Authors: Shanbhag, Pramod, Nareddy, Pradeep R, Dadwal, Mamta, Mobin, Shaikh M, Namboothiri, Irishi N N
Format: Article
Language:English
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Summary:Reaction of nitroalkenes or nitrodienes with methyl vinyl ketone (MVK) or acrylate in the presence of the imidazole-LiCl catalyst system provides Rauhut-Currier (vinylogous Morita-Baylis-Hillman) adducts in moderate yield. Under similar conditions (imidazole-hydroquinone), nitroalkenes and nitrodienes undergo self-dimerization to afford the Rauhut-Currier adducts in varying yields. An alternative self-dimerization-nitro group elimination pathway in the presence tricyclohexylphosphine was observed with heteroaromatic nitroalkenes. A synthetically useful one-pot two step transformation of Rauhut-Currier adducts of nitroalkenes with MVK to 2,3-disubstituted cyclopentenones is also described.
ISSN:1477-0520
1477-0539
DOI:10.1039/c0ob00062k