Chelucci, Giorgio Adolfo and Marchetti, Mauro and Malkov, Andrei V. and Friscourt, Frédéric and Swarbrick, Martin E. and Kocovsky, Pavel (2011) New monoterpene-derived phosphinopyridine ligands and their application in the enantioselective iridium-catalyzed hydrogenation. Tetrahedron, Vol. 67 (30), p. 5421-5431. ISSN 0040-4020. Article.
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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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