Diastereoselective synthesis of an argatroban intermediate, ethyl (2R, 4R)-4-methylpipecolate, by means of a Mandyphos/rhodium complex-catalyzed hydrogenation

P Ferraboschi, M De Mieri, P Grisenti, M Lotz…

Index: Ferraboschi, Patrizia; Mieri, Maria De; Grisenti, Paride; Lotz, Matthias; Nettekoven, Ulrike Tetrahedron Asymmetry, 2011 , vol. 22, # 16-17 p. 1626 - 1631

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Citation Number: 7

Abstract

The synthetic antithrombotic argatroban is a dipeptide between the nonproteogenic (2R, 4R)- 4-methyl-2-piperidine carboxylic acid and l-arginine, in turn bonded to a methyltetrahydroquinoline sulfonyl group. An extensive screening of transition metal-based complexes with different ligands was performed in order to identify the best catalyst for the diastereoselective hydrogenation of a suitable 4, 5-dehydropiperidine precursor aimed ...