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
Full Text: HTML
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. ...
Related Articles:
Highly active iridium (i) complexes for the selective hydrogenation of carbon–carbon multiple bonds
[Bennie, Linsey S.; Fraser, Calum J.; Irvine, Stephanie; Kerr, William J.; Andersson, Shalini; Nilsson, Goeran N. Chemical Communications, 2011 , vol. 47, # 42 p. 11653 - 11655]
[Louis, Simon N.; Nero, Tracy L.; Iakovidis, Dimitri; Colagrande, Felicia M.; Jackman, Graham P.; Louis, William J. European Journal of Medicinal Chemistry, 1999 , vol. 34, # 11 p. 919 - 937]
[Kashanna, Jajula; Jangili, Paramesh; Kumar, Rathod Aravind; Das, Biswanath Helvetica Chimica Acta, 2012 , vol. 95, # 9 p. 1666 - 1671]