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 the suitable 4,5-dehydropiperidine aimed towards the synthesis of the (2R,4R)-4-methyl piperidine moiety.
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, U. Nettekoven. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 22:16-17(2011), pp. 1626-1631. [10.1016/j.tetasy.2011.09.009]
Diastereoselective Synthesis of an Argatroban Intermediate, Ethyl (2R,4R)-4-methylpipecolate, by means of a Mandyphos/Rhodium Complex-catalyzed Hydrogenation
P. FerraboschiPrimo
;M. De MieriSecondo
;
2011
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 the suitable 4,5-dehydropiperidine aimed towards the synthesis of the (2R,4R)-4-methyl piperidine moiety.Pubblicazioni consigliate
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