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

Literature Information

Publication Date 2010-08-24
DOI 10.1039/C0OB00062K
Impact Factor 3.876
Authors

Pramod Shanbhag, Pradeep R. Nareddy, Mamta Dadwal, Shaikh M. Mobin, Irishi N. N. Namboothiri


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Abstract

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.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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