Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

被引：631

作者：

Cheng, Qiang ^{[1
]}

Tu, Hang-Fei ^{[1
]}

Zheng, Chao ^{[1
]}

Qu, Jian-Ping ^{[2
]}

Helmchen, Guenter ^{[3
]}

You, Shu-Li ^{[1
]}

机构：

[1] Univ Chinese Acad Sci, Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

[2] Nanjing Tech Univ, Jiangsu Natl Synerget Innovat Ctr Adv Mat, Sch Chem & Mol Engn, Inst Adv Synth, Nanjing 211816, Jiangsu, Peoples R China

[3] Heidelberg Univ, Organ Chem Inst Ruprecht Karls, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

来源：

CHEMICAL REVIEWS | 2019年 / 119卷 / 03期

基金：

中国国家自然科学基金; 国家重点研发计划;

关键词：

HETEROCYCLIC CARBENE COMPLEX; CROSS-COUPLING REACTIONS; ALPHA-AMINO-ACIDS; ENANTIOSELECTIVE MODULAR SYNTHESIS; AMINATION/RING-CLOSING METATHESIS; TETRAHYDRO-BETA-CARBOLINES; IR/ZN DUAL CATALYSIS; STEREOSELECTIVE-SYNTHESIS; DEAROMATIZATION REACTION; PHOSPHORAMIDITE LIGAND;

D O I：

10.1021/acs.chemrev.8b00506

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this review, we summarize the origin and advancements of iridium catalyzed asymmetric allylic substitution reactions during the past two decades. Since the first report in 1997, Ir-catalyzed asymmetric allylic substitution reactions have attracted intense attention due to their exceptionally high regio- and enantioselectivities. Ir-catalyzed asymmetric allylic substitution reactions have been significantly developed in recent years in many respects, including ligand development, mechanistic understanding, substrate scope, and application in the synthesis of complex functional molecules. In this review, an explicit outline of ligands, mechanism, scope of nucleophiles, and applications is presented.

引用

页码：1855 / 1969

页数：115

共 414 条

[81] Construction of Enantioenriched Cyclic Compounds by Asymmetric Allylic Alkylation and Ring-Closing Metathesis [J].

Giacomina, Francesca ;

Alexakis, Alexandre .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (29) :6710-6721

[82] ω-Ethylenic Allylic Substrates as Alternatives to Cyclic Substrates in Copper- and Iridium-Catalyzed Asymmetric Allylic Alkylation [J].

Giacomina, Francesca ;

Riat, David ;

Alexakis, Alexandre .

ORGANIC LETTERS, 2010, 12 (06) :1156-1159

[83] Enantioselective Iridium-Catalyzed Allylic Aminations of Allylic Carbonates with Functionalized Side Chains. Asymmetric Total Synthesis of (S)-Vigabatrin [J].

Gnamm, Christian ;

Franck, Geraldine ;

Miller, Nicole ;

Stork, Timon ;

Broedner, Kerstin ;

Helmchen, Guenter .

SYNTHESIS-STUTTGART, 2008, 20 (20) :3331-3350

[84] Enantioselective iridium-catalyzed allylic alkylations -: Improvements and applications based on salt-free reaction conditions [J].

Gnamm, Christian ;

Foerster, Sebastian ;

Miller, Nicole ;

Broedner, Kerstin ;

Helmchen, Guenter .

SYNLETT, 2007, (05) :790-794

[85] A Configurational Switch Based on Iridium-Catalyzed Allylic Cyclization: Application in Asymmetric Total Syntheses of Prosopis, Dendrobate, and Spruce Alkaloids [J].

Gnamm, Christian ;

Broedner, Kerstin ;

Krauter, Caroline M. ;

Helmchen, Guenter .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (40) :10514-10532

[86] Stereoselective Synthesis of 2,6-Disubstituted Piperidines Using the Iridium-Catalyzed Allylic Cyclization as Configurational Switch: Asymmetric Total Synthesis of (+)-241D and Related Piperidine Alkaloids [J].

Gnamm, Christian ;

Krauter, Caroline M. ;

Broedner, Kerstin ;

Helmchen, Guenter .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (09) :2050-2054

[87] Corboxylic acids as substrates in homogeneous catalysts [J].

Goossen, Lukas J. ;

Rodriguez, Nuria ;

Goossen, Kathe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (17) :3100-3120

[88] Iridium-catalyzed regio- and enantioselective allylation of ketone enolates [J].

Graening, T ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) :17192-17193

[89] Enantio- and Diastereoselective Spiroketalization Catalyzed by Chiral Iridium Complex [J].

Hamilton, James Y. ;

Roessler, Simon L. ;

Carreira, Erick M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (24) :8082-8085

[90] Iridium-Catalyzed Enantioselective Allylic Alkylation with Functionalized Organozinc Bromides [J].

Hamilton, James Y. ;

Sarlah, David ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (26) :7644-7647

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