Synfacts 2006(12): 1259-1259  
DOI: 10.1055/s-2006-955635
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Synthesis of Chiral Aryl Glycines

Contributor(s): Mark Lautens, Yann Béthuel
G. Shang, Q. Yang, X. Zhang*
The Pennsylvania State University, University Park, USA
Further Information

Publication History

Publication Date:
22 November 2006 (online)

Significance

Chiral aryl glycines are biologically relevant compounds that received a great deal of attention over the last years. They can be prepared by aminohydroxylation (K. L. Reddy, K. B. Sharpless J. Am. Chem. Soc. 1998, 120, 1207-1217), amination of enolates (D. A. Evans, S. G. Nelson J. Am. Chem. Soc. 1997, 119, 6452-6453) or reductive amination (R. Kadyrov, T. H. Riermeier, U. Dingerdissen, V. Tararov, A. Börner J. Org. Chem. 2003, 68, 4067-4070) but in some cases low regioselectivity, high catalyst loading or poor reactivity is observed. The authors applied their recently developed TangPhos ligand (Angew. Chem. Int. Ed. 2002, 41, 1612-1614) to the enantioselective hydrogenation of a variety of α-imino esters.