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Enzyme-Inspired Chiral Secondary-Phosphine-Oxide Ligand with Dual Noncovalent Interactions for Asymmetric Hydrogenation |
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| Authors: | Caiyou Chen Zhefan Zhang Shicheng Jin Dr Xiangru Fan Mingyu Geng Yan Zhou Songwei Wen Xinrui Wang Dr Lung Wa Chung Dr Xiu-Qin Dong Prof Xumu Zhang |
| Institution: | 1. College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P.R. China;2. Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518000 P.R. China;3. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China |
| Abstract: | Inspired by the unique character of enzymes, we developed novel chiral SPO (secondary-phosphine-oxide) ligand (SPO-Wudaphos) which can enter into both ion pair and H-bond noncovalent interactions. The novel chiral SPO-Wudaphos exhibited excellent results in the asymmetric hydrogenation of α-methylene-γ-keto carboxylic acids, affording the chiral γ-keto acids with up to over 99 % ee. A series of control experiments and DFT calculations were conducted to illustrate the critical roles of both the ion pair and H-bond noncovalent interactions. |
| Keywords: | asymmetric hydrogenations ferrocene derivatives noncovalent interactions phosphine ligands γ-keto acids |