Enantioselective Organocatalytic Direct Aldol Reactions of α-Oxyaldehydes: Step One in a Two-Step Synthesis of Carbohydrates

Authors

  • Alan B. Northrup,

    1. Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd., MC 164–30, Pasadena CA 91125, USA, Fax: (+1) 626-795-3658
    Search for more papers by this author
  • Ian K. Mangion,

    1. Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd., MC 164–30, Pasadena CA 91125, USA, Fax: (+1) 626-795-3658
    Search for more papers by this author
  • Frank Hettche,

    1. Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd., MC 164–30, Pasadena CA 91125, USA, Fax: (+1) 626-795-3658
    Search for more papers by this author
  • David W. C. MacMillan Prof.

    1. Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd., MC 164–30, Pasadena CA 91125, USA, Fax: (+1) 626-795-3658
    Search for more papers by this author

  • The authors wish to thank Amgen, AstraZeneca, Bristol–Myers Squibb, Johnson and Johnson, Eli Lilly, and Merck Research Laboratories for financial support. F.H. is grateful for a DFG post-doctoral fellowship. A.B.N. and I.K.M. are grateful for NSF predoctoral fellowships.

Abstract

original image

Two-faced: α-Oxyaldehydes can act as both an aldol donor and an aldol acceptor and can be coupled enantioselectively by using proline as the reaction catalyst. This new aldol reaction provides an operationally simple protocol for the stereocontrolled production of erythrose (see scheme) architecture and sets the stage for a two-step enantioselective synthesis of carbohydrates.

Ancillary