Disulfonimide-Catalyzed Asymmetric Vinylogous and Bisvinylogous Mukaiyama Aldol Reactions

Authors

  • Lars Ratjen,

    1. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
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  • Dr. Pilar García-García,

    1. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
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  • Frank Lay,

    1. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
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  • Dr. Michael Edmund Beck,

    1. Bayer CropScience AG, Alfred-Nobel-Strasse 50, 40789 Monheim am Rhein (Germany)
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  • Prof. Dr. Benjamin List

    Corresponding author
    1. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
    • Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
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  • We thank Caroline Gawlik for technical support. Furthermore, help from our analytical departments, especially the NMR, HPLC, and MS facilities is gratefully acknowledged. We thank Sanofi-Aventis, the Max-Planck-Society, the DFG (Priority Program Organocatalysis SPP1179), and the Fonds der Chemischen Industrie for funding.

Abstract

original image

Let's talk about six! A new chiral disulfonimide catalyzed vinylogous Mukaiyama aldol addition of crotonic acid derived nucleophiles to aldehydes has been developed and the concept of vinylogy was further expanded to double vinylogous, sorbic acid derived nucleophiles. This reaction is an example of a previously unknown ε-selective bisvinylogous Mukaiyama Aldol addition that extends the substrate by six carbon atoms (see scheme).

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