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Open AccessArticle

Computational Prediction of Chiral Iron Complexes for Asymmetric Transfer Hydrogenation of Pyruvic Acid to Lactic Acid

by Wan Wang 1,2,3 and Xinzheng Yang 1,2,3,*
1
State Key Laboratory for Structural Chemistry of Unstable and Stable Species, Institute of Chemistry Chinese Academy of Sciences, Beijing 100190, China
2
University of Chinese Academy of Sciences, Beijing 100049, China
3
Beijing National Laboratory for Molecular Sciences, CAS Research/Education Center for Excellence in Molecular Sciences, Beijing 100190, China
*
Author to whom correspondence should be addressed.
Academic Editor: Hans-Joachim Knölker
Molecules 2020, 25(8), 1892; https://doi.org/10.3390/molecules25081892
Received: 29 February 2020 / Revised: 13 April 2020 / Accepted: 13 April 2020 / Published: 20 April 2020
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
Density functional theory calculations reveal a formic acid-assisted proton transfer mechanism for asymmetric transfer hydrogenation of pyruvic acid catalyzed by a chiral Fe complex, FeH[(R,R)-BESNCH(Ph)CH(Ph)NH2](η6-p-cymene), with formic acid as the hydrogen provider. The rate-determining step is the hydride transfer from formate anion to Fe for the formation and dissociation of CO2 with a total free energy barrier of 28.0 kcal mol−1. A series of new bifunctional iron complexes with η6-p-cymene replaced by different arene and sulfonyl groups were built and computationally screened as potential catalysts. Among the proposed complexes, we found 1g with η6-p-cymene replaced by 4-isopropyl biphenyl had the lowest free energy barrier of 26.2 kcal mol−1 and excellent chiral selectivity of 98.5% ee. View Full-Text
Keywords: asymmetric transfer hydrogenation; density functional theory; bifunctional catalyst asymmetric transfer hydrogenation; density functional theory; bifunctional catalyst
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Wang, W.; Yang, X. Computational Prediction of Chiral Iron Complexes for Asymmetric Transfer Hydrogenation of Pyruvic Acid to Lactic Acid. Molecules 2020, 25, 1892.

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