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Bulky Achiral Triarylphosphines Mimic BINAP in Ru(II)‐ Catalyzed Asymmetric Hydrogenation of Ketones
Author(s) -
Jing Qing,
Zhang Xue,
Sun Jie,
Ding Kuiling
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505054
Subject(s) - chemistry , enantiopure drug , enantioselective synthesis , asymmetric hydrogenation , phosphine , denticity , steric effects , catalysis , binap , noyori asymmetric hydrogenation , optically active , diamine , organic chemistry , combinatorial chemistry , crystal structure
In the present work, we report on catalysis of the enantioselective hydrogenation of ketones with Ru(II) complexes composed of cheap achiral monodentate phosphine ligands in combination with an enantiopure 1,2‐diamine, affording a variety of optically active secondary alcohols with high efficiency and enantioselectivity. The steric impact of achiral monophosphine ligands in Ru complexes was found to be a critical factor for the high enantioselectivity of the reaction. This finding throws some light on a long‐standing challenge, the high cost of chiral bisphosphine ligands, associated with an industrial application of the asymmetric hydrogenation of ketones.