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Issue 22, 2011
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Regioselective and stereoselective cyclizations of cyclohexadienones tethered to active methylene groups

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Abstract

The cyclization of 2,5-cyclohexadienones tethered to activated methylene groups was studied. The substitution around the cyclohexadienone ring serves to regioselectively direct these cyclizations based primarily on electronic effects. In the case of brominated substrates, these reactions proceed to give highly unusual electron-deficient tricyclic cyclopropanes. By using a Cinchona alkaloid-based phase-transfer catalyst, prochiral cyclohexadienones can be desymmetrized with moderate stereoselectivity.

Graphical abstract: Regioselective and stereoselective cyclizations of cyclohexadienones tethered to active methylene groups

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Supplementary files

Article information


Submitted
08 Jul 2011
Accepted
09 Aug 2011
First published
10 Aug 2011

Org. Biomol. Chem., 2011,9, 7849-7859
Article type
Paper

Regioselective and stereoselective cyclizations of cyclohexadienones tethered to active methylene groups

R. Tello-Aburto, K. A. Kalstabakken, K. A. Volp and A. M. Harned, Org. Biomol. Chem., 2011, 9, 7849
DOI: 10.1039/C1OB06125A

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