Combined organo- and gold-catalyzed enantioselective synthesis of bicyclic enones

Theo Zweifel, Dirk Hollmann, Birgit Prüger, Martin Nielsen, Karl Anker Jørgensen

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32 Citations (Scopus)

Abstract

By combining organocatalysis with gold catalysis highly enantioenriched bicyclic enones are available via an operationally simple one-pot procedure. Iminium-ion activation by cinchona alkaloid-derived primary amine catalysts induces the Michael addition of propargylated malononitriles and cyanoacetates to α,β-unsaturated ketones. The resulting intermediates undergo an exo-dig cyclization, forming a new C-C bond followed by double-bond isomerization to give highly functionalized bicyclic enones in good yields and high enantioselectivities.

Original languageEnglish
JournalTetrahedron Asymmetry
Volume21
Issue11-12
Pages (from-to)1624-1629
Number of pages6
ISSN0957-4166
DOIs
Publication statusPublished - 23 Jun 2010

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