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Issue 31, 2014
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Enantioselective palladium catalyzed conjugate additions of ortho-substituted arylboronic acids to β,β-disubstituted cyclic enones: total synthesis of herbertenediol, enokipodin A and enokipodin B

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Abstract

The palladium-catalyzed conjugate addition (Michael addition) of ortho-substituted arylboronic acids to β,β-disubstituted cyclic enones, in particular 3-methyl cyclopent-2-enone and 3-methyl cyclohex-2-enone, is reported. With an achiral bipyridine-based palladium catalyst, good yields are obtained with a variety of ortho-substituted arylboronic acids. In the asymmetric version, good to very high enantiomeric excesses (up to 99% ee) are obtained, though the yields are moderate. The decreased yields are attributed to significant protodeboronation of the arylboronic acid. The developed methodology allows the efficient enantioselective synthesis of the very crowded, biologically active, sesquiterpenes herbertenediol, enokipodin A, and enokipodin B.

Graphical abstract: Enantioselective palladium catalyzed conjugate additions of ortho-substituted arylboronic acids to β,β-disubstituted cyclic enones: total synthesis of herbertenediol, enokipodin A and enokipodin B

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Publication details

The article was received on 26 May 2014, accepted on 20 Jun 2014 and first published on 23 Jun 2014


Article type: Paper
DOI: 10.1039/C4OB01085J
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 5883-5890
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    Enantioselective palladium catalyzed conjugate additions of ortho-substituted arylboronic acids to β,β-disubstituted cyclic enones: total synthesis of herbertenediol, enokipodin A and enokipodin B

    J. Buter, R. Moezelaar and A. J. Minnaard, Org. Biomol. Chem., 2014, 12, 5883
    DOI: 10.1039/C4OB01085J

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