Mechanistic insights into asymmetric transfer hydrogenation of pyruvic acid catalysed by chiral osmium complexes with formic acid assisted proton transfer†
Wan
Wang 
ab
and
Xinzheng
Yang
*ab
ab
and
Xinzheng
Yang
*ab
Abstract
A density functional theory study of the asymmetric transfer hydrogenation of pyruvic acid to ł- and D-lactic acids catalysed by a chiral osmium complex OsH[(R,R)TsNCH(Ph)CH(Ph)NH2](η6-p-cymene) reveals a formic acid assisted enantio-determining proton-coupled hydride transfer mechanism. Activation strain model analysis indicates that the C–H/π interaction between η6-arene and carboxyl ligands has a significant influence on the enantioselectivity. The replacement of p-cymene by 4-isopropyl biphenyl or phenyl is highly likely to improve the catalytic performance of the complex.
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