On the Development of Catalytic
Carba-6π Electrocyclizations

Lee M. Bishop; Russell E. Roberson; Robert G. Bergman; Dirk Trauner

doi:10.1055/s-0029-1218812

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Synthesis 2010(13): 2233-2244
DOI: 10.1055/s-0029-1218812

PAPER

On the Development of Catalytic Carba-6π Electrocyclizations

Lee M. Bishop^a, Russell E. Roberson^b, Robert G. Bergman*^a, Dirk Trauner*^c
^a Department of Chemistry, University of California, Berkeley, CA 94720-1460, USA
Fax: +1(510)6427714; e-Mail: rbergman@berkeley.edu;
^b Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA
^c Department of Chemistry, Ludwig Maximilians-Universität, Munich 81377, Germany
Fax: +49(892)18077972; e-Mail: dirk.trauner@cup.uni-muenchen.de;

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Publication History

Received 5 May 2010
Publication Date:
08 June 2010 (online)

Abstract
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Abstract

Hexatriene substrates substituted in the 2-position with carbonyl groups were studied in the context of catalytic 6p electrocyclizations. The nature of the carbonyl group and the substitution pattern on the hexatriene have significant effects on the ability of these substrates to succumb to catalysis. A novel 2-formyl hexatriene dimerization was observed. The first example of a catalytic asymmetric carba-6p electrocyclization is reported along with the discovery of an unusual kinetic resolution via a catalytic photochemical electrocyclic ring-opening.

Key words

electrocyclic reactions - catalysis - dimerization - asymmetric catalysis - kinetic resolution.

Supporting Information

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Supplementary Material

Supporting Information