Facile construction of three contiguous stereogenic centers via dynamic kinetic resolution in asymmetric transfer hydrogenation of quinolines

被引：52

作者：

Chen, Mu-Wang ^{[1
]}

Cai, Xian-Feng ^{[1
]}

Chen, Zhang-Pei ^{[1
]}

Shi, Lei ^{[1
]}

Zhou, Yong-Gui ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 83期

基金：

中国国家自然科学基金;

关键词：

IRIDIUM-CATALYZED HYDROGENATION; ORGANOCATALYTIC TRANSFER HYDROGENATION; HIGHLY ENANTIOSELECTIVE HYDROGENATION; BRONSTED ACID; HETEROAROMATIC-COMPOUNDS; HANTZSCH ESTERS; DIASTEREOSELECTIVE SYNTHESIS; SECONDARY ALCOHOLS; AMINO-ALCOHOLS; EFFICIENT;

D O I：

10.1039/c4cc06060a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient and facile route to chiral tetrahydroquinolines with three contiguous stereogenic centers via a dynamic kinetic resolution process has been successfully developed by using chiral phosphoric acid as catalyst and Hantzsch ester as the hydrogen source with up to 89% ee.

引用

页码：12526 / 12529

页数：4

共 64 条

[11] Asymmetric hydrogenation of aromatic compounds [J].

Glorius, F .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (23) :4171-4175

[12] Iridium-Catalyzed Asymmetric Hydrogenation of Quinoline Derivatives with C3*-TunePhos [J].

Gou, Fa-Rong ;

Li, Wei ;

Zhang, Xumu ;

Liang, Yong-Min .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (14-15) :2441-2444

[13] The development of double axially chiral phosphoric acids and their catalytic transfer hydrogenation of quinolines [J].

Guo, Qun-Sheng ;

Du, Da-Ming ;

Xu, Jiaxi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (04) :759-762

[14] Chiral Phosphoric Acid Catalyzed Inverse-Electron-Demand Aza-Diels-Alder Reaction of Isoeugenol Derivatives [J].

He, Long ;

Bekkaye, Mathieu ;

Retailleau, Pascal ;

Masson, Geraldine .

ORGANIC LETTERS, 2012, 14 (12) :3158-3161

[15] Asymmetric Hydrogenation of β-Keto Sulfonamides and β-Keto Sulfones with a Chiral Cationic Ruthenium Diamine Catalyst [J].

Huang, Xiao-Fei ;

Zhang, Shao-Yun ;

Geng, Zhi-Cong ;

Kwok, Chun-Yuen ;

Liu, Peng ;

Li, Hai-Yan ;

Wang, Xing-Wang .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (14-15) :2860-2872

[16] Catalytic asymmetric hydrogenation of α-ketoesters and quinoline using electronically enriched BINAP [J].

Jahjah, Mohamad ;

Alame, Mohamad ;

Pellet-Rostaing, Phane ;

Lemaire, Marc .

TETRAHEDRON-ASYMMETRY, 2007, 18 (19) :2305-2312

[17] Organocatalytic Aza-Michael-Michael Cascade Reactions: A Flexible Approach to 2,3,4-Trisubstituted Tetrahydroquinolines [J].

Jia, Zhen-Xin ;

Luo, Yong-Chun ;

Wang, Yao ;

Chen, Liang ;

Xu, Peng-Fei ;

Wang, Binghe .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (41) :12958-12961

[18] Highly Enantioselective Synthesis of Polysubstituted Tetrahydroquinolines via Organocatalytic Michael/Aza-Henry Tandem Reactions [J].

Jia, Zhen-Xin ;

Luo, Yong-Chun ;

Xu, Peng-Fei .

ORGANIC LETTERS, 2011, 13 (05) :832-835

[19] Ionic-Surfactant-Coated Burkholderia cepacia Lipase as a Highly Active and Enantioselective Catalyst for the Dynamic Kinetic Resolution of Secondary Alcohols [J].

Kim, Hyunjin ;

Choi, Yoon Kyung ;

Lee, Jusuk ;

Lee, Eungyeong ;

Park, Jaiwook ;

Kim, Mahn-Joo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (46) :10944-10948

[20] Chemoenzymatic Dynamic Kinetic Resolution of Alcohols and Amines [J].

Lee, Jin Hee ;

Han, Kiwon ;

Kim, Mahn-Joo ;

Park, Jaiwook .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (06) :999-1015

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