Highly efficient synthesis of B-amino acid derivatives via asymmetric hydrogenation of unprotected enamines

ORGN 614

Yi Hsiao1, Nelo R. Rivera1, Thorsten Rosner1, Shane W. Krska1, Eugenia Njolito1, Fang Wang2, Yongkui Sun1, Joseph D. Armstrong III1, Edward J. J. Grabowski1, and Richard D. Tillyer1. (1) Department of Process Research, Merck Research Laboratories, PO Box 2000, Rahway, NJ 07065, (2) Department of Analytical Research, Merck Research Laboratories, PO Box 2000, Rahway, NJ 07065
A direct asymmetric hydrogenation of unprotected enamino esters and amides is described. Catalyzed by Rh complexes with Josiphos type chiral ligands, this method gives B-amino esters and amides in high yield and high ee (93–97 %ee). No acyl protection/deprotection is required.

 

New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004