Synfacts 2005(2): 0251-0251  
DOI: 10.1055/s-2005-916123
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of β-Substituted β-Amino Esters

Contributor(s): Paul Knochel, Andrei Gavryushin
A. K. Awasthi*, M. L. Boys, K. J. Cain-Janicki, P.-J. Colson, W. W. Doubleday, J. E. Duran, P. N. Farid
Pfizer, Inc., Ann Arbor, USA
Further Information

Publication History

Publication Date:
25 October 2005 (online)

Significance

The article describes a practical large-scale enantioselective synthesis of β-aminoesters from corresponding aldehydes, using chiral phenylglycinol as a chiral auxiliary. The 1,2-addition to the imines formed from an aldehyde and phenylglycinol proceeds with high diastereoselectivity. The products are important subunits of many biologically active compounds. The authors also reported a useful multikilogram-scale protocol for the preparation of the Reformatsky reagent (BrZnCH2CO2 t-Bu×THF).