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|Title: ||Rauhut-Currier type homo- and heterocouplings involving nitroalkenes and nitrodienes|
|Authors: ||SHANBHAG, P|
|Keywords: ||baylis-hillman reaction|
|Issue Date: ||2010|
|Publisher: ||ROYAL SOC CHEMISTRY|
|Citation: ||ORGANIC & BIOMOLECULAR CHEMISTRY, 8(21), 4867-4873|
|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.|
|Appears in Collections:||Article|
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