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Studies on cycloaddition reactions of 2,2-dimethyl-3,4-dihydro-2H-pyrrole N-oxide and N-(benzylidene)methylamine N-oxide with alpha,beta-unsaturated lactones & esters

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Title Studies on cycloaddition reactions of 2,2-dimethyl-3,4-dihydro-2H-pyrrole N-oxide and N-(benzylidene)methylamine N-oxide with alpha,beta-unsaturated lactones & esters
 
Creator BASKARAN, S
BASKARAN, C
NADKARNI, PJ
TRIVEDI, GK
CHANDRASEKHAR, J
 
Subject 1,3-dipolar cycloadditions
cyclo-additions
nitrones
reactivity
selectivity
1-oxide
 
Description Intermolecular asymmetric 1,3-dipolar cycloaddition of 2,2-dimethyl-3,4-dihydro-2H- pyrrole N-oxide and N-(benzylidene)methylamine N-oxide with optically active alpha,beta-unsaturated esters 1,2,4 and 7-9 provided the corresponding diastereomers while chiral sugar lactones gave stereoselectively the cycloadducts 17a and 17b (in the case of dipolarophile 3) and 18 in (the case of the dipolarophile 6) with the acyclic nitrone B. The stereochemistry of the products has been established using high field nmr techniques. The regioselectivities of these reactions are inconsistent with FMO coefficients and are explained on the basis of charge distribution obtained through AM1 calculations. (C) 1997 .
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2011-08-26T17:16:26Z
2011-12-26T12:57:32Z
2011-12-27T05:43:00Z
2011-08-26T17:16:26Z
2011-12-26T12:57:32Z
2011-12-27T05:43:00Z
1997
 
Type Article
 
Identifier TETRAHEDRON, 53(20), 7057-7076
0040-4020
http://dx.doi.org/10.1016/S0040-4020(97)00403-1
http://dspace.library.iitb.ac.in/xmlui/handle/10054/11384
http://hdl.handle.net/10054/11384
 
Language en