Efficient preparation of an N-aryl β-amino acid via asymmetric hydrogenation and direct asymmetric reductive amination en route to Ezetimibe

…, B de Lange, Y Okamura, Y Yusa, K Matsumura…

Index: Busscher, Guuske F.; Lefort, Laurent; Cremers, Jozef G.O.; Mottinelli, Marco; Wiertz, Roel W.; Lange, Ben De; Okamura, Yutaka; Yusa, Yukinori; Matsumura, Kazuhiko; Shimizu, Hideo; De Vries, Johannes G.; De Vries, Andre H.M. Tetrahedron Asymmetry, 2010 , vol. 21, # 13-14 p. 1709 - 1714

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Citation Number: 21

Abstract

Two routes for the preparation of an N-aryl β-amino acid, an important precursor for the cholesterol-lowering drug Ezetimibe, were investigated. The first pathway proceeds via an Rh-or Ir-catalyzed asymmetric hydrogenation of N-aryl enamine giving the desired product with up to 82% ee. The other pathway involves a direct asymmetric reductive amination (DARA) of the β-keto ester which yielded the β-amino ester in high yield and 97% ee. ...

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