DSpace
 

DSpace at IIT Bombay >
IITB Publications >
Review >

Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/100/2988

Title: Morita-baylis-hillman reactions between conjugated nitroalkenes or nitrodienes and carbonyl compounds
Authors: DEB, I
SHANBHAG, P
MOBIN, SM
NAMBOOTHIRI, INN
Keywords: alkenes
alpha-hydroxyalkylation
c-c coupling
nitroalkenes
morita-baylis-hillman (mbh) reaction
synthetic methods
Issue Date: 2009
Publisher: WILEY-V C H VERLAG GMBH
Citation: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,(24)4091-4101
Abstract: Morita-Baylis-Hillman (MBH) reactions between conjugated nitroalkenes or nitrodienes and various carbonyl compounds such as glyoxylate, trifluoropyruvate, pyruvaldehyde, oxomalonate, ninhydrin, and formaldehyde have been extensively investigated. The reactions proceeded smoothly in the presence of DMAP (40-100 mol-%) in acetonitrile and in some cases also in that of imidazole (100 mol-%) in CHCl(3) or THF, to provide the multifunctional adducts in good to excellent yields. The reactions catalyzed by DMAP in acetonitrile were superior to the imidazole-catalyzed reactions both in terms of the rate of reaction and in terms of the isolated yields of the MBH adducts. The catalytic roles played by DMAP and imidazole in these reactions, vis-a-vis other MBH catalysts such as DABCO, are attributed primarily to resonance stabilization of the initial zwitterionic intermediates. Whereas the E isomers are the major or exclusive products in the cases of glyoxylate, pyruvaldehyde, and formaldehyde, the Z isomers predominate in the cases of trifluoropyruvate and ninhydrin. Interestingly, oxomalonate forms E isomers with aromatic nitroalkenes and Z isomers with aliphatic ones. These selectivities and the formation of unusual deconjugated products in the case of certain beta-alkyl-nitroethylenes have been explained. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
URI: http://dx.doi.org/10.1002/ejoc.200900475
http://dspace.library.iitb.ac.in/xmlui/handle/10054/13755
http://hdl.handle.net/100/2988
ISSN: 1434-193X
Appears in Collections:Review

Files in This Item:

There are no files associated with this item.

View Statistics

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

 

Valid XHTML 1.0! DSpace Software Copyright © 2002-2010  Duraspace - Feedback