Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

被引：593

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：

国家重点研发计划; 中国国家自然科学基金;

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

[1] Stereoisomerically Pure Trisubstituted Vinylaluminum Reagents and their Utility in Copper-Catalyzed Enantioselective Synthesis of 1,4-Dienes Containing Z or E Alkenes
Akiyama, Katsuhiro
Gao, Fang
Hoveyda, Amir H.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (02) : 419 - 423
[2] Alamgir M, 2007, TOP HETEROCYCL CHEM, V9, P87, DOI 10.1007/7081_2007_088
[3] Highly enantioselective copper(I)-phosphoramidite-catalysed additions of organoaluminium reagents to enones
Alexakis, A
Albrow, V
Biswas, K
d'Augustin, M
Prieto, O
Woodward, S
[J]. CHEMICAL COMMUNICATIONS, 2005, (22) : 2843 - 2845
[4] Very efficient phosphoramidite ligand for asymmetric iridium-catalyzed allylic alkylation
Alexakis, A
Polet, D
[J]. ORGANIC LETTERS, 2004, 6 (20) : 3529 - 3532
[5] Iridium-catalyzed asymmetric allylic substitution with aryl zinc reagents
Alexakis, Alexandre
El Hajjaji, Samir
Polet, Damien
Rathgeb, Xavier
[J]. ORGANIC LETTERS, 2007, 9 (17) : 3393 - 3395
[6] [Anonymous], 2016, ASYMMETRIC DEAROMATI
[7] Highly enantioselective synthesis of tetrahydro-β-carbolines and tetrahydro-γ-carbolines via Pd-catalyzed intramolecular allylic alkylation
Bandini, M
Melloni, A
Piccinelli, F
Sinisi, R
Tommasi, S
Umani-Ronchi, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) : 1424 - 1425
[8] New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic subsitution: Controlling the regioselectivity
Bandini, M
Melloni, A
Umani-Ronchi, A
[J]. ORGANIC LETTERS, 2004, 6 (18) : 3199 - 3202
[9] Bao C.-C., 2018, ORGANOMETALLICS, DOI [10.1021/acs.orga-nomet.8b00762, DOI 10.1021/ACS.ORGA-NOMET.8B00762]
[10] Bartels B, 2003, EUR J ORG CHEM, V2003, P1097

← 1 2 3 4 5 6 7 8 9 10 →