Rh-Catalyzed Highly Enantioselective Hydrogenation of Functionalized Olefins with Chiral Ferrocenylphosphine-Spiro Phosphonamidite Ligands

被引：8

作者：

Chen, Yirui ^{[1
]}

Yi, Xiao ^{[1
]}

Cheng, Yuqi ^{[1
]}

Huang, An ^{[1
]}

Yang, Zehui ^{[1
]}

Zhao, Xianghua ^{[1
]}

Ling, Fei ^{[1
]}

Zhong, Weihui ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 12期

基金：

中国国家自然科学基金;

关键词：

PHOSPHINE-PHOSPHORAMIDITE LIGANDS; DYNAMIC KINETIC RESOLUTION; ASYMMETRIC HYDROGENATION; PHOSPHORUS LIGANDS; PRACTICAL LIGANDS; RHODIUM COMPLEX; MECHANISM; AMINES; ENAMIDES; ESTERS;

D O I：

10.1021/acs.joc.2c00532

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient Rh-catalyzed hydrogenation of functionalized olefins has been realized by a new family of highly rigid chiral ferrocenylphosphine-spiro phosphonamidite ligands. Excellent enantiocontrol (>99% ee in most cases) was achieved with a wide range of alpha-dehydroamino acid esters and alpha-enamides. This practicable catalytic system was further applied in the scalable synthesis of highly optically pure key intermediates of cinacalcet and D-phenylalanine.

引用

页码：7864 / 7874

页数：11

共 60 条

[1] Chemoenzymatic synthesis of boron-containing chiral amines and amides [J].

Andrade, Leandro H. ;

Barcellos, Thiago ;

Santiago, Carolina G. .

TETRAHEDRON-ASYMMETRY, 2010, 21 (19) :2419-2424

[2] Transition-Metal-Catalyzed Asymmetric Hydrogenation and Transfer Hydrogenation: Sustainable Chemistry to Access Bioactive Molecules [J].

Ayad, Tahar ;

Phansavath, Phannarath ;

Ratovelomanana-Vidal, Virginie .

CHEMICAL RECORD, 2016, 16 (06) :2754-2771

[3] Phosphinoferrocenylaminophosphines as novel and practical ligands for asymmetric catalysis [J].

Boaz, NW ;

Debenham, SD ;

Mackenzie, EB ;

Large, SE .

ORGANIC LETTERS, 2002, 4 (14) :2421-2424

[4] Hybrid bidentate phosphoramidite ligands in asymmetric catalysis [J].

Boeda, Fabien ;

Beneyton, Thomas ;

Crevisy, Christophe .

MINI-REVIEWS IN ORGANIC CHEMISTRY, 2008, 5 (02) :96-127

[5] Silver-Promoted Direct Phosphorylation of Bulky C(sp2)-H Bond to Build Fully Substituted β-Phosphonodehydroamino Acids [J].

Cao, Hao-Qiang ;

Liu, Hao-Nan ;

Liu, Zhe-Yuan ;

Qiao, Baokun ;

Zhang, Fa-Guang ;

Ma, Jun-An .

ORGANIC LETTERS, 2020, 22 (16) :6414-6419

[6] Chiral phosphine-phosphoramidite ligands in asymmetric catalysis [J].

Chen, Xiu-Shuai ;

Hou, Chuan-Jin ;

Hu, Xiang-Ping .

SYNTHETIC COMMUNICATIONS, 2016, 46 (11) :917-941

[7]

Crabtree R.H., 2007, COMPREHENSIVE ORGANO

[8] Asymmetric Reduction of Aromatic α-Dehydroamino Acid Esters with Water as Hydrogen Source [J].

Dai, Yuze ;

Chen, Jingchao ;

Wang, Zheting ;

Wang, Ting ;

Wang, Lin ;

Yang, Yong ;

Qiao, Xingfang ;

Fan, Baomin .

JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (10) :7141-7147

[9] BINOL-derived phosphoramidites in asymmetric hydrogenation: can the presence of a functionality in the amino group influence the catalytic outcome? [J].

Eberhardt, Luc ;

Armspach, Dominique ;

Harrowfield, Jack ;

Matt, Dominique .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (04) :839-864

[10]

Enders D, 1998, EUR J ORG CHEM, V1998, P689, DOI 10.1002/(SICI)1099-0690(199804)1998:4<689::AID-EJOC689>3.0.CO

← 1 2 3 4 5 6 →