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A stereoselective and atom-efficient approach to multifunctionalized five- and six-membered rings via a novel michael-initiated intramolecular Diels-Alder furan reaction

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Title A stereoselective and atom-efficient approach to multifunctionalized five- and six-membered rings via a novel michael-initiated intramolecular Diels-Alder furan reaction
 
Creator NAMBOOTHIRI, IRISHI NN
GANESH, MADHU
SHAIKH, MOBIN M
COJOCARU, MIRIAM
 
Subject addition reactions
molecular dynamics
two dimensional
thermal effects
x-ray crystallography
 
Description A variety of key precursors to the intramolecular Diels-Alder reaction of furan diene (IMDAF) have been prepared via a very facile 1,4-addition of O-, S-, N-, and C-centered nucleophiles possessing
unsaturated tether to รข-furyl nitroethylene. Subsequent IMDAF reaction of the 1,4-adducts, carried out under thermal conditions, provided five- and six-membered carbocycles and heterocycles fused to an easily cleavable oxabicycloheptene moiety. The structure and stereochemistry of the
cycloadducts were determined by 2D-NMR experiments and further confirmed by X-ray crystallography. The salient features of the strategy include high degree of stereoselectivity (>80:20) in
the cycloaddition, atom and step economy, and generation of multiple chiral centers and
functionalities. The feasibility of the cleavage of the oxa bridge in the cycloadducts to afford novel
multifunctional molecules has also been demonstrated.
 
Publisher American Chemical Society
 
Date 2009-02-25T12:21:48Z
2011-11-25T17:52:33Z
2011-12-26T13:06:25Z
2011-12-27T05:54:14Z
2009-02-25T12:21:48Z
2011-11-25T17:52:33Z
2011-12-26T13:06:25Z
2011-12-27T05:54:14Z
2005
 
Type Article
 
Identifier Journal of Organic Chemistry 70(6), 2235-2243,
0022-3263
http://dx.doi.org/10.1021/jo048262x
http://hdl.handle.net/10054/781
http://dspace.library.iitb.ac.in/xmlui/handle/10054/781
 
Language en