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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/11384

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
Authors: BASKARAN, S
BASKARAN, C
NADKARNI, PJ
TRIVEDI, GK
CHANDRASEKHAR, J
Keywords: 1,3-dipolar cycloadditions
cyclo-additions
nitrones
reactivity
selectivity
1-oxide
Issue Date: 1997
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Citation: TETRAHEDRON, 53(20), 7057-7076
Abstract: 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 .
URI: 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
ISSN: 0040-4020
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