3 years ago

Enzyme-Inspired Chiral Secondary-Phosphine-Oxide Ligand with Dual Noncovalent Interactions for Asymmetric Hydrogenation

Enzyme-Inspired Chiral Secondary-Phosphine-Oxide Ligand with Dual Noncovalent Interactions for Asymmetric Hydrogenation
Shicheng Jin, Xumu Zhang, Mingyu Geng, Lung Wa Chung, Songwei Wen, Xiu-Qin Dong, Xiangru Fan, Yan Zhou, Caiyou Chen, Zhefan Zhang, Xinrui Wang
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. Two different interactions: Just like enzymes which can enter into multiple cooperative noncovalent interactions with substrates, the chiral secondary-phosphine-oxide (SPO) Wudaphos ligand can engage in ion pair and H-bonding interactions. The chiral SPO-Wudaphos ligand gave excellent results in the rhodium-catalyzed asymmetric hydrogenation of α-methylene-γ-keto carboxylic acids.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201701394

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