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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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Publication details

The article was received on 08 Jul 2011, accepted on 09 Aug 2011 and first published on 10 Aug 2011


Article type: Paper
DOI: 10.1039/C1OB06125A
Citation: Org. Biomol. Chem., 2011,9, 7849-7859
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    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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