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New monoterpene-derived phosphinopyridine ligands and their application in the enantioselective iridium-catalyzed hydrogenation |
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| Authors: | Giorgio Chelucci Mauro MarchettiAndrei V Malkov Frédéric Friscourt Martin E SwarbrickPavel Ko?ovský |
| Institution: | a Dipartimento di Chimica, Università di Sassari, Via Vienna 2, I-07100 Sassari, Italy b Istituto di Chimica Biomolecolare-CNR, Traversa La Crucca 3-Baldinca, I-07040 Sassari, Italy c Department of Chemistry, WestChem, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK d Neurology Centre of Excellence for Drug Discovery, GlaxoSmithKline, Harlow CM19 5AW, UK |
| 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). |
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