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NH/π Attraction: A Role in Asymmetric Hydrogenation of Aromatic Ketones with Binap/1,2‐Diamine‐Ruthenium(II) Complexes
Author(s) -
Sandoval Christian A.,
Shi Qixun,
Liu Shasha,
Noyori Ryoji
Publication year - 2009
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200900171
Subject(s) - substituent , ketone , ruthenium , asymmetric hydrogenation , chemistry , diamine , attraction , medicinal chemistry , catalysis , stereochemistry , organic chemistry , enantioselective synthesis , philosophy , linguistics
Role model : Electrostatic NH eq /π attraction plays an important role in asymmetric hydrogenation of acetophenones catalyzed by chiral [RuX 2 (diphosphine)(1,2‐diamine)] complexes. The relative rate of p ‐substituted ketones bears a Hammett linear relationship with ρ =1.03 but with a notable exception for the p ‐fluoro ketone. The enantioselectivity is enhanced by an electron‐donating p substituent and is decreased by an electron donor.