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Cycloaddition between electron deficient partners: an efficient regio- and stereoselective synthesis of functionalised bicyclo[2.2.2]octenones. A tandem alkylation, stereochemical inversion and aldol condensation

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Title Cycloaddition between electron deficient partners: an efficient regio- and stereoselective synthesis of functionalised bicyclo[2.2.2]octenones. A tandem alkylation, stereochemical inversion and aldol condensation
 
Creator SINGH, VISHWAKARMA
PRAVEENA, GD
SHAIKH, MOBIN M
 
Subject spiroepoxycyclohexa-2,4-dienones
cycloaddition
bicyclo[2.2.2]octenones
 
Description A novel one step regio- and stereoselective synthesis of functionalised bicyclo[2.2.2]octenones from readily available aromatic precursors is described. The methodology involved in situ generation of reactive spiroepoxycyclohexadienones and π4s+π2s cycloaddition with methyl vinyl ketone. Study on π-facial alkylation that led to the formation of homobrendane derivatives as a result of stereochemical inversion and aldol condensation in tandem, is also presented. The crystal structure of 6-acetyl-1-methoxy-bicyclo[2.2.2]oct-7-en-2-one-spiro[3,2′]oxirane and 3-methoxy-4,6,9-trimethyltricyclo[4.3.1.03,7]decan-8-en-5-one-spiro[2,2′]oxirane is also reported.
 
Publisher Elsevier
 
Date 2009-02-20T07:29:20Z
2011-11-25T17:37:31Z
2011-12-26T13:06:27Z
2011-12-27T05:54:17Z
2009-02-20T07:29:20Z
2011-11-25T17:37:31Z
2011-12-26T13:06:27Z
2011-12-27T05:54:17Z
2004
 
Type Article
 
Identifier Tetrahedron 60(19), 4177-4182
0040-4020
http://dx.doi.org/10.1016/j.tet.2004.03.051
http://hdl.handle.net/10054/721
http://dspace.library.iitb.ac.in/xmlui/handle/10054/721
 
Language en