Phosphine-mediated [4 + 2] annulation of bis(enones): a Lewis base catalyzed "mock Diels-Alder" reaction |
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| Authors: | Couturier Michel Ménard Fréderic Ragan John A Riou Maxime Dauphin Etienne Andresen Brian M Ghosh Arun Dupont-Gaudet Kristina Girardin Mélina |
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| Institution: | Chemical Research and Development, Pfizer Global Research and Development, Eastern Point Road, P.O. Box 8013, Groton, CT 06340-8013, USA. michel_a_couturier@groton.pfizer.com |
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| Abstract: | Lewis-base-catalyzed cycloisomerization of bis(enones) to decalins has been demonstrated as an alternative to the traditional Lewis acid catalyzed Diels-Alder cycloaddition. In this process, a trialkylphosphine mediates both bond formation steps in two distinct catalytic cycles. The single-pot operation generates two carbon-carbon bonds and up to five contiguous stereocenters in one step, starting from achiral, aliphatic substrates; eight examples are provided. reaction: see text] |
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