Preparation and Asymmetric Hydrogenation of β-Aryl-Substituted β-Acylaminoacrylates

Authors

  • Jingsong You Dr.,

    1. Institut für Organische Katalyseforschung an der Universität Rostock e. V., Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383
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  • Hans-Joachim Drexler Dr.,

    1. Institut für Organische Katalyseforschung an der Universität Rostock e. V., Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383
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  • Songlin Zhang Dr.,

    1. Institut für Organische Katalyseforschung an der Universität Rostock e. V., Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383
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  • Christine Fischer Dr.,

    1. Institut für Organische Katalyseforschung an der Universität Rostock e. V., Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383
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  • Detlef Heller Priv.-Doz. Dr.

    1. Institut für Organische Katalyseforschung an der Universität Rostock e. V., Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383
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  • We thank the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie for the generous support of this work. We are grateful to Dr. R. McCague and Dr. A. Zanotti-Gerosa of ChiroTech for catalysts and ligands.

Abstract

original image

The Rh-catalyzed asymmetric hydrogenation of β-aryl-substituted (E)-β-acylaminoacrylates, which were isolated for the first time, with, for example [Rh{(R,R)-(Et-FerroTANE)}(nbd)]+ as catalyst (see picture) proceeds under very mild conditions (25 °C, normal pressure) and high substrate/catalyst ratios with very good enantioselectivity (Et-FerroTANE=(+)-1,1′-bis(2,4-diethylphosphyltane)ferrocene, nbd=3,5-norbornadiene).

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