This work was supported by the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie, the Bundesministerium für Forschung und Technologie (Aids-Forschungsförderung im Bundesgesundheitsamt) and Bayer AG. We thank Dr. Häbich for helpful discussions and Ms. Petra Schneider for experimental help. Results of these investigations were presented in Hamburg, Germany, at the Org.-Chem. Kolloquium, November 30th, 1990, and in Oxford, Great Britain, at the 13th International Symposium “Synthesis in Organic Chemistry”, Perkin Division, RSC, July 20–22, 1993.
Article first published online: 22 DEC 2003
Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany
Angewandte Chemie International Edition in English
Volume 33, Issue 12, pages 1298–1301, June 6, 1994
How to Cite
Franz, T., Hein, M., Veith, U., Jäger, V., Peters, E.-M., Peters, K. and von Schnering, H. G. (1994), Simple and Versatile Synthesis of Optically Active 1,2-Amino Alcohols by Grignard Addition to N,O-Dibenzylglyceraldimine and -lactaldimine. Angew. Chem. Int. Ed. Engl., 33: 1298–1301. doi: 10.1002/anie.199412981
Dedicated to Professor Ulrich Schmidt on the occasion of his 70th birthday
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 6 DEC 1993
In many cases with high threo selectivity, Grignard additions can be performed on simple, nonactivated, and even enolizable imine derivatives of optically active aldehydes, as the reactions with 1 and 2 show. This should open a new route to aminohydroxy acids that supplements the familiar one starting from α-amino acids/aldehydes.