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
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Creator |
SINGH, VISHWAKARMA
PRAVEENA, GD SHAIKH, MOBIN M |
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Subject |
spiroepoxycyclohexa-2,4-dienones
cycloaddition bicyclo[2.2.2]octenones |
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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.
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Publisher |
Elsevier
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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 |
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Type |
Article
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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 |
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Language |
en
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