Catalytic Asymmetric Transfer Hydrogenation of Imines: Recent Advances

被引：66

作者：

Foubelo, Francisco ^{[1
,2
]}

Yus, Miguel ^{[1
,2
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

[2] Univ Alicante, Ctr Innovac Quim Avanzada ORFEO CINQA, E-03080 Alicante, Spain

来源：

CHEMICAL RECORD | 2015年 / 15卷 / 05期

关键词：

asymmetric synthesis; homogeneous catalysis; hydrogen transfer; imines; organocatalysis; DYNAMIC KINETIC RESOLUTION; BETA-AMINO ALCOHOLS; ENANTIOSELECTIVE SYNTHESIS; REDUCTIVE AMINATION; STEREOSELECTIVE-SYNTHESIS; IRON CATALYSTS; ACID; EFFICIENT; LIGANDS; KETONES;

D O I：

10.1002/tcr.201500203

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this review article recent developments in the asymmetric transfer hydrogenation of imines from 2008 up to today are presented. The main methodology involves either metal-catalyzed procedures in the presence of a chiral ligand or organocatalyzed technologies using a Hantzsch ester and a chiral BINOL-derived phosphoric acid. The most important procedures are collected, paying special attention to the application of this methodology in synthetic organic chemistry.

引用

页码：907 / 924

页数：18

共 88 条

[1]

[Anonymous], 2008, MODERN REDUCTION MET

[2] Industrial methods for the production of optically active intermediates [J].

Breuer, M ;

Ditrich, K ;

Habicher, T ;

Hauer, B ;

Kesseler, M ;

Stürmer, R ;

Zelinski, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (07) :788-824

[3] Chiral Phosphoric Acid-Catalyzed Asymmetric Transfer Hydrogenation of Quinolin-3-amines [J].

Cai, Xian-Feng ;

Guo, Ran-Ning ;

Feng, Guang-Shou ;

Wu, Bo ;

Zhou, Yong-Gui .

ORGANIC LETTERS, 2014, 16 (10) :2680-2683

[4] Asymmetric Transfer Hydrogenation of 3-Nitroquinolines: Facile Access to Cyclic Nitro Compounds with Two Contiguous Stereocenters [J].

Cai, Xian-Feng ;

Chen, Mu-Wang ;

Ye, Zhi-Shi ;

Guo, Ran-Ning ;

Shi, Lei ;

Li, Yan-Qin ;

Zhou, Yong-Gui .

CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (07) :1381-1385

[5] Facile construction of three contiguous stereogenic centers via dynamic kinetic resolution in asymmetric transfer hydrogenation of quinolines [J].

Chen, Mu-Wang ;

Cai, Xian-Feng ;

Chen, Zhang-Pei ;

Shi, Lei ;

Zhou, Yong-Gui .

CHEMICAL COMMUNICATIONS, 2014, 50 (83) :12526-12529

[6] Microwave-Assisted Solvent-Free Synthesis of Enantiomerically Pure N-(tert-Butylsulfinyl)imines [J].

Collados, Juan F. ;

Toledano, Estefania ;

Guijarro, David ;

Yus, Miguel .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (13) :5744-5750

[7] Use of α-chlorinated N-(tert-butanesulfinyl)-imines in the synthesis of chiral aziridines [J].

Denolf, Bram ;

Mangelinckx, Sven ;

Tornroos, Karl W. ;

De Kimpe, Norbert .

ORGANIC LETTERS, 2006, 8 (14) :3129-3132

[8]

desVries J. G., 2011, CATAL SCI TECHNOL, V1, P727

[9] Phenylene-Coated Magnetic Nanoparticles that Boost Aqueous Asymmetric Transfer Hydrogenation Reactions [J].

Gao, Xiaoshuang ;

Liu, Rui ;

Zhang, Dacheng ;

Wu, Meng ;

Cheng, Tanyu ;

Liu, Guohua .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (06) :1515-1519

[10] Synthesis of Highly Enantiomerically Enriched Amines by Asymmetric Transfer Hydrogenation of N-(tert-Butylsulfinyl) Imines [J].

Guijarro, David ;

Pablo, Oscar ;

Yus, Miguel .

ORGANIC SYNTHESES, 2013, 90 :338-+

← 1 2 3 4 5 6 7 8 9 →