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Enzyme‐Inspired Chiral Secondary‐Phosphine‐Oxide Ligand with Dual Noncovalent Interactions for Asymmetric Hydrogenation
Author(s) -
Chen Caiyou,
Zhang Zhefan,
Jin Shicheng,
Fan Xiangru,
Geng Mingyu,
Zhou Yan,
Wen Songwei,
Wang Xinrui,
Chung Lung Wa,
Dong XiuQin,
Zhang Xumu
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201701394
Subject(s) - non covalent interactions , chemistry , phosphine oxide , ligand (biochemistry) , asymmetric hydrogenation , stereochemistry , phosphine , tandem , enzyme , oxide , amino acid , combinatorial chemistry , enantioselective synthesis , organic chemistry , materials science , molecule , hydrogen bond , catalysis , receptor , biochemistry , composite material
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.