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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
Authors
GD PRAVEENA
MOBIN M SHAIKH
VISHWAKARMA SINGH
Publication date
1 January 2004
Publisher
'Elsevier BV'
Doi
Cite
Abstract
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.© Elsevie
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Last time updated on 15/05/2019