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.
Enantioselective Organocatalytic Direct Aldol Reactions of α-Oxyaldehydes: Step One in a Two-Step Synthesis of Carbohydrates†
Article first published online: 22 MAR 2004
Copyright © 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 43, Issue 16, pages 2152–2154, April 13, 2004
How to Cite
Northrup, A. B., Mangion, I. K., Hettche, F. and MacMillan, D. W. C. (2004), Enantioselective Organocatalytic Direct Aldol Reactions of α-Oxyaldehydes: Step One in a Two-Step Synthesis of Carbohydrates. Angew. Chem. Int. Ed., 43: 2152–2154. doi: 10.1002/anie.200453716
- Issue published online: 6 APR 2004
- Article first published online: 22 MAR 2004
- Manuscript Received: 9 JAN 2004
- aldol reaction;
- homogeneous catalysis
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.