Double Asymmetric Hydrogenation of α-Iminoketones: Facile Synthesis of Enantiopure Vicinal Amino Alcohols

被引：16

作者：

Wang, Jiang ^{[1
,2
,3
]}

Lin, Xin ^{[1
,2
,4
]}

Shao, Pan-Lin ^{[1
,2
,4
]}

Song, Jingyuan ^{[1
,2
]}

Wen, Jialin ^{[1
,2
,5
]}

Zhang, Xumu ^{[1
,2
]}

机构：

[1] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China

[2] Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China

[3] Peking Univ, Sch Chem Biol & Biotechnol, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China

[4] Southern Univ Sci & Technol, Coll Innovat & Entrepreneurship, Shenzhen 518055, Peoples R China

[5] Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518055, Peoples R China

来源：

ACS CATALYSIS | 2021年 / 11卷 / 20期

基金：

中国国家自然科学基金;

关键词：

asymmetric hydrogenation; DuanPhos; alpha-iminoketones; vicinal amino alcohols; stepwise transformation; CATALYZED ENANTIOSELECTIVE HYDROGENATION; KETONES; LIGANDS; IMINES; ROUTE; CONSTRUCTION; REAGENT; ACCESS; ESTERS;

D O I：

10.1021/acscatal.1c03635

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

This study presents an Rh/DuanPhos-catalyzed double asymmetric hydrogenation of alpha-iminoketones for accessing chiral vicinal amino alcohols, which are privileged motifs in pharmaceuticals, agrochemicals, fine chemicals, chiral auxiliaries, organocatalysts, etc. Compared with existing methods, this methodology has the following advantages, such as one-pot operation, high efficiency, operational simplicity, limited waste, broad reaction scope, and high yields (90 to 96%) and stereoselectivities (up to >99:1 dr; >99.9% ee). In addition, the mechanism of the transformation was revealed to be a stepwise reaction by isolating and analyzing reaction intermediates.

引用

页码：12729 / 12735

页数：7

共 71 条

[1] Synthesis of enantiopure syn-beta-amino alcohols. A simple case of chelation-controlled additions of diethylzinc to alpha-(dibenzylamino) aldehydes [J].

Andres, JM ;

Barrio, R ;

Martinez, MA ;

Pedrosa, R ;

PerezEncabo, A .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4210-4213

[2] B-[(E)-3-(DIPHENYLAMINO)ALLYL]DIISOPINOCAMPHEYLBORANE - AN EXCELLENT REAGENT FOR THE STEREOSELECTIVE SYNTHESIS OF ANTI-BETA-DIPHENYLAMINO ALCOHOLS [J].

BARRETT, AGM ;

SEEFELD, MA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (04) :339-341

[3] Convenient asymmetric syntheses of anti-beta-amino alcohols [J].

Barrett, AGM ;

Seefeld, MA ;

White, AJP ;

Williams, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) :2677-2685

[4] Design and Synthesis of Chiral oxa-Spirocyclic Ligands for Ir-Catalyzed Direct Asymmetric Reduction of Bringmann's Lactones with Molecular H2 [J].

Chen, Gen-Qian ;

Lin, Bi-Jin ;

Huang, Jia-Ming ;

Zhao, Ling-Yu ;

Chen, Qi-Shu ;

Jia, Shi-Peng ;

Yin, Qin ;

Zhang, Xumu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (26) :8064-8068

[5] Evolution of a Manufacturing Route to Omarigliptin, A Long-Acting DPP-4 Inhibitor for the Treatment of Type 2 Diabetes [J].

Chung, John Y. L. ;

Scott, Jeremy P. ;

Anderson, Camille ;

Bishop, Brian ;

Bremeyer, Nadine ;

Cao, Yang ;

Chen, Qmghao ;

Dunn, Robert ;

Kassim, Amude ;

Lieberman, David ;

Moment, Aaron J. ;

Sheen, Faye ;

Zacuto, Michael .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (11) :1760-1768

[6] Recent Developments in Methodology for the Direct Oxyamination of Olefins [J].

Donohoe, Timothy J. ;

Callens, Cedric K. A. ;

Flores, Aida ;

Lacy, Adam R. ;

Rathi, Akshat H. .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (01) :58-76

[7] Recent Developments in Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution [J].

Echeverria, Pierre-Georges ;

Ayad, Tahar ;

Phansavath, Phannarath ;

Ratovelomanana-Vidal, Virginie .

SYNTHESIS-STUTTGART, 2016, 48 (16) :2523-2539

[8] Application of chiral mixed phosphorus/sulfur ligands to enantioselective rhodium-catalyzed dehydroamino acid hydrogenation and ketone hydrosilylation processes [J].

Evans, DA ;

Michael, FE ;

Tedrow, JS ;

Campos, KR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) :3534-3543

[9] Asymmetric ring opening of meso-epoxides with aromatic amines catalyzed by a new proline-based N,N′-dioxide-indium tris(triflate) complex [J].

Gao, Bo ;

Wen, Yuehong ;

Yang, Zhigang ;

Huang, Xiao ;

Liu, Xiaohua ;

Feng, Xiaoming .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) :385-390

[10] Rhodium-catalyzed Asymmetric Hydrogenation of -Dehydroamino Ketones: A General Approach to Chiral -amino Ketones [J].

Gao, Wenchao ;

Wang, Qingli ;

Xie, Yun ;

Lv, Hui ;

Zhang, Xumu .

CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (02) :231-233

← 1 2 3 4 5 6 7 8 →