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

被引：23

作者：

Chelucci, Giorgio ^{[1
]}

Marchetti, Mauro ^{[2
]}

Malkov, Andrei V. ^{[3
]}

Friscourt, Frederic ^{[3
]}

Swarbrick, Martin E. ^{[4
]}

Kocovsky, Pavel ^{[3
]}

机构：

[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

[2] CNR, Ist Chim Biomol, I-07040 Sassari, Italy

[3] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

[4] GlaxoSmithKline, Neurol Ctr Excellence Drug Discovery, Harlow CM19 5AW, Essex, England

来源：

TETRAHEDRON | 2011年 / 67卷 / 30期

关键词：

N-S LIGANDS; ASYMMETRIC ALLYLIC SUBSTITUTION; HIGHLY-ACTIVE CATALYST; CHIRAL LIGANDS; 1,10-PHENANTHROLINE LIGANDS; 2-AMINO-2'-DIPHENYLPHOSPHINO-1,1'-BINAPHTHYL MAP; (ETA(3)-ALLYL)PALLADIUM COMPLEXES; 2,2'/6',2''-TERPYRIDINE LIGANDS; DIPYRIDYLMETHANE LIGANDS; PALLADIUM(II) COMPLEXES;

D O I：

10.1016/j.tet.2011.05.075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyridine derivatives with a phosphine or phosphinite pendant ( 1 11) have been synthesized from (+)-alpha-pinene, (-)-isopinocampheol, and/or (+)-camphor via Krohnke 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). (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：5421 / 5431

页数：11

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