New monoterpene-derived phosphinopyridine ligands and their application in the enantioselective iridium-catalyzed hydrogenation

Chelucci, G., Marchetti, M., Malkov, A.V., Friscourt, F., Swarbrick, M.E. and Kočovský, P. (2011) New monoterpene-derived phosphinopyridine ligands and their application in the enantioselective iridium-catalyzed hydrogenation. Tetrahedron, 67(30), pp. 5421-5431. (doi: 10.1016/j.tet.2011.05.075)

Abstract

Pyridine derivatives with a phosphine or phosphinite pendant (1–11) have been synthesized from (⁺)-α-pinene, (⁻)-isopinocampheol, and/or (⁺)-camphor via Kröhnke annulation or another annulation method as the key step for the construction of the pyridine nucleus. The iridium complex of 6 proved to catalyze hydrogenation of the prochiral unfunctionalized alkene 44 with 94% ee, whereas the complex of 2 was most efficient in the hydrogenation of the cinnamyl-type ester 45 (83% ee).

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Malkov, Dr Andrei and Kocovsky, Professor Pavel
• Authors: Chelucci, G., Marchetti, M., Malkov, A.V., Friscourt, F., Swarbrick, M.E., and Kočovský, P.
• Subjects: Q Science > QD Chemistry
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Tetrahedron
• ISSN: 0040-4020
• ISSN (Online): 1464-5416