A New Motif for Lewis Base Catalysis: Asymmetric Reduction of β-Enamino Esters

Authors

  • Dr. Andreas Weickgenannt,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-83-36501
    Search for more papers by this author
  • Prof. Dr. Martin Oestreich

    Corresponding author
    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-83-36501
    2. Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin (Germany), Fax: (+49) 30-314-29745
    • Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-83-36501
    Search for more papers by this author

Abstract

original image

Reduced to the basics: Activation of Lewis acidic Cl3SiH with chiral amide-based Lewis bases allows for the stereocontrolled reduction of several types of β-enamino esters (see scheme). By this, the new motif of α-acetoxy β-enamino esters is transformed into α-hydroxy β-amino acids, a transformation still unknown in transition metal-catalyzed hydrogenation. PMP=4-methoxyphenyl.

Ancillary