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

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Title Rauhut-Currier type homo- and heterocouplings involving nitroalkenes and nitrodienes
 
Creator SHANBHAG, P
NAREDDY, PR
DADWAL, M
MOBIN, SM
NAMBOOTHIRI, INN
 
Subject baylis-hillman reaction
pauson-khand reaction
alpha,beta-unsaturated nitro-compounds
dabco-catalyzed dimerization
conjugated nitroalkenes
anticancer activity
michael cycloisomerization
activated olefins
acrylic compounds
esters
 
Description 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.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2011-08-28T16:13:54Z
2011-12-26T12:58:06Z
2011-12-27T05:47:27Z
2011-08-28T16:13:54Z
2011-12-26T12:58:06Z
2011-12-27T05:47:27Z
2010
 
Type Article
 
Identifier ORGANIC & BIOMOLECULAR CHEMISTRY, 8(21), 4867-4873
1477-0520
http://dx.doi.org/10.1039/c0ob00062k
http://dspace.library.iitb.ac.in/xmlui/handle/10054/11784
http://hdl.handle.net/10054/11784
 
Language en