Redox of ferrocene controlled asymmetric dehydrogenative Heck reaction via palladium-catalyzed dual C-H bond activation

被引：168

作者：

Pi, Chao ^{[1
]}

Li, Ying ^{[1
]}

Cui, Xiuling ^{[1
,2
]}

Zhang, Hao ^{[1
]}

Han, Yanbing ^{[1
]}

Wu, Yangjie ^{[1
]}

机构：

[1] Zhengzhou Univ, Key Lab Appl Chem Henan Univ, Dept Chem, Henan Key Lab Chem Biol & Organ Chem, Zhengzhou 450052, Peoples R China

[2] Huaqiao Univ, Engn Res Ctr Mol Med, Chinese Educ Minist, Xiamen Key Lab Ocean & Gene Drugs,Inst Mol Med, Xiamen 361021, Fujian, Peoples R China

来源：

CHEMICAL SCIENCE | 2013年 / 4卷 / 06期

关键词：

PLANAR-CHIRAL FERROCENES; HIGHLY ENANTIOSELECTIVE SYNTHESIS; ELECTRON-DEFICIENT ARENES; KINETIC RESOLUTION; STEREOSELECTIVE SYNTHESES; ORTHO-LITHIATION; DERIVATIVES; OLEFINATION; LIGANDS; AMINO;

D O I：

10.1039/c3sc50577d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel strategy of dehydrogenative Heck reaction controlled by redox process of ferrocene has been developed. Commercially available chiral amino acid as ligand realized asymmetric dehydrogenative Heck reaction, leading to planar-chiral ferrocene derivatives with excellent enantioselectivity and in good to excellent yields (up to 99% ee and 98% yield).

引用

页码：2675 / 2679

页数：5

共 93 条

[1] Kinetic Resolution: A Powerful Tool for the Synthesis of Planar-Chiral Ferrocenes [J].

Alba, Andrea-Nekane R. ;

Rios, Ramon .

MOLECULES, 2009, 14 (11) :4747-4757

[2] Enantioselective Palladium-Catalyzed Direct Arylations at Ambient Temperature: Access to Indanes with Quaternary Stereocenters [J].

Albicker, Martin R. ;

Cramer, Nicolai .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9139-9142

[3] Enantioselective synthesis of 2-methyl indolines by palladium catalysed asymmetric C(sp3)-H activation/cyclisation [J].

Anas, Saithalavi ;

Cordi, Alex ;

Kagan, Henri B. .

CHEMICAL COMMUNICATIONS, 2011, 47 (41) :11483-11485

[4] Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products [J].

Antonchick, Andrey P. ;

Gerding-Reimers, Claas ;

Catarinella, Mario ;

Schuermann, Markus ;

Preut, Hans ;

Ziegler, Slava ;

Rauh, Daniel ;

Waldmann, Herbert .

NATURE CHEMISTRY, 2010, 2 (09) :735-740

[5] Catalytic Asymmetric Synthesis of Planar-Chiral Transition-Metal Complexes [J].

Arae, Sachie ;

Ogasawara, Masamichi .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2012, 70 (06) :593-605

[6] Recent applications of chiral ferrocene ligands in asymmetric catalysis [J].

Arrayas, Ramon Gomez ;

Adrio, Javier ;

Carretero, Juan Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (46) :7674-7715

[7] The syntheses and catalytic applications of unsymmetrical ferrocene ligands [J].

Atkinson, RCJ ;

Gibson, VC ;

Long, NJ .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (05) :313-328

[8] STEREOSELECTIVE SYNTHESES .8. ABSOLUTE CONFIGURATION OF A 1,2-DISUBSTITUTED FERROCENE DERIVATIVE WITH PLANAR AND CENTRAL ELEMENTS OF CHIRALITY AND MECHANISM OF STEREOSELECTIVE METALATIONS OF OPTICALLY-ACTIVE ALPHA-FERROCENYL TERTIARY-AMINES [J].

BATTELLE, LF ;

BAU, R ;

GOKEL, GW ;

OYAKAWA, RT ;

UGI, IK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :482-486

[9] Mechanistic Rationalization of Unusual Kinetics in Pd-Catalyzed C-H Olefination [J].

Baxter, Ryan D. ;

Sale, David ;

Engle, Keary M. ;

Yu, Jin-Quan ;

Blackmond, Donna G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (10) :4600-4606

[10]

Blaser H.-U., 2008, Ferrocenes: Ligands, Materials and Biomolecules, P205

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