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

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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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:	Article
ID Code:	6219
Status:	Published
Refereed:	Yes
Uncontrolled Keywords:	Ligand synthesis, pyridine-type, phosphine, phosphinite, iridium complexes
Subjects:	Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:	001 Università di Sassari > 01 Dipartimenti > Chimica 002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:	Pergamon / Elsevier
ISSN:	0040-4020
Copyright Holders:	© 2011 Elsevier Ltd.
Deposited On:	06 Jul 2011 11:27

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