Rhodium-Catalyzed Asymmetric Hydrogenation of 3-Benzoylaminocoumarins for the Synthesis of Chiral 3-Amino Dihydrocoumarins

被引：25

作者：

Xu, Yunnan ^{[1
]}

Liu, Delong ^{[1
]}

Deng, Yu ^{[1
]}

Zhou, Yi ^{[1
]}

Zhang, Wanbin ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Shanghai Key Lab Mol Engn Chiral Drugs, Sch Pharm, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

[2] Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 44期

基金：

中国国家自然科学基金;

关键词：

3-amino dihydrocoumarins; asymmetric hydrogenation; chirality; cyclic amino acid derivatives; rhodium; ENANTIOSELECTIVE SYNTHESES; BIOLOGICAL EVALUATION; DIPHOSPHINE LIGANDS; PHOSPHORUS LIGANDS; AMINO-ACIDS; INHIBITORS; DERIVATIVES; DISCOVERY; MECHANISM; INDOLINE;

D O I：

10.1002/anie.202110286

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An asymmetric hydrogenation of 3-benzoylaminocoumarins was achieved for the first time using our BridgePhos-Rh catalytic system, providing chiral 3-amino dihydrocoumarins in high yields (up to 98 %) and with excellent enantioselectivities (up to 99.7 % ee). The relationship between the enantioselectivities of the hydrogenations and the dihedral angles and the resulting pi-pi stacking effects of the BridgePhos-Rh complexes, which were determined by X-ray diffraction analysis, are discussed. The corresponding hydrogenated products allow for many transformations, providing several chiral skeletons with important physiological and pharmacological activities.

引用

页码：23602 / 23607

页数：6

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