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Dynamic kinetic resolution catalyzed by Ir axially chiral phosphine catalyst: asymmetric synthesis of anti aromatic beta-hydroxy-alpha-amino acid esters.

Research paper by Kazuishi K Makino, Yasuhiro Y Hiroki, Yasumasa Y Hamada

Indexed on: 21 Apr '05Published on: 21 Apr '05Published in: Journal of the American Chemical Society



Abstract

The anti selective hydrogenation of alpha-amino-beta-keto esters via dynamic kinetic resolution was achieved for the first time by using the iridium-MeOBIPHEP catalyst in asymmetric synthesis of anti aromatic beta-hydroxy-alpha-amino acid esters with excellent diastereo- and enantioslectivities. Acetic acid as a solvent and sodium acetate as an additive affected dramatically the yield and the enantioselectivity, respectively. The product anti aromatic beta-hydroxy-alpha-amino acid esters are useful for synthesis of pharmaceuticals and natural products.