Progress in Iridium-Catalyzed Asymmetric Allylic Substitution Reactions with Allylic Esters

被引：14

作者：

Deng, Yingying ^{[1
]}

Yang, Wen ^{[1
]}

Yang, Xin ^{[1
]}

Yang, Dingqiao ^{[1
]}

机构：

[1] South China Normal Univ, Sch Chem & Environm, Minist Educ, Key Lab Theoret Chem Environm, Guangzhou 510006, Guangdong, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 37卷 / 12期

基金：

中国国家自然科学基金;

关键词：

iridium catalyst; allylic esters; asymmetric allylic substitution; nucleophile; recent research progress; ENANTIOSELECTIVE SYNTHESIS; DEAROMATIZATION REACTION; ALPHA-ALLYLATION; ANION EQUIVALENTS; VICINAL TERTIARY; SALT-FREE; ALKYLATION; REGIO; AMINATION; ENANTIO;

D O I：

10.6023/cjoc201704034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iridium-catalyzed asymmetric allylic substitution reaction is one of the most important methods for the synthesis of chiral compounds. The recent research progress in iridium-catalyzed asymmetric allylic substitution reactions of allylic ester and its derivatives is reviewed with focus on the influences of the iridium catalysts, the substrate structures of allylic ester and its derivatives, the type of nucleophiles, the effects of solvents and additives on asymmetric substitution reaction. Moreover, the possible mechanisms are also discussed in this review.

引用

页码：3039 / 3059

页数：21

共 103 条

[1] 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
[2] Rhodium-Catalyzed Dynamic Kinetic Asymmetric Transformations of Racemic Tertiary Allylic Trichloroacetimidates with Anilines
Arnold, Jeffrey S.
Nguyen, Hien M.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (20) : 8380 - 8383
[3] Natural Products as Inspiration for Reaction Development: Catalytic Enantioselective Decarboxylative Reactions of Prochiral Enolate Equivalents
Behenna, Douglas C.
Stoltz, Brian M.
[J]. INVENTING REACTIONS, 2013, 44 : 281 - 313
[4] Application of iridium catalyzed allylic substitution reactions in the synthesis of branched tryptamines and homologues via tandem hydroformylation-Fischer indole synthesis
Bondzic, Bojan P.
Farwick, Andreas
Liebich, Jens
Eilbracht, Peter
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (20) : 3723 - 3731
[5] Formaldehyde N,N-Dialkylhydrazones as Neutral Formyl Anion Equivalents in Iridium-Catalyzed Asymmetric Allylic Substitution
Breitler, Simon
Carreira, Erick M.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (16) : 5296 - 5299
[6] Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates
Butt, Nicholas A.
Zhang, Wanbin
[J]. CHEMICAL SOCIETY REVIEWS, 2015, 44 (22) : 7929 - 7967
[7] Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles
Chen, Ming
Hartwig, John F.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (38) : 11651 - 11655
[8] Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides
Chen, Ming
Hartwig, John F.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (43) : 13972 - 13979
[9] Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Silyl Dienolates Derived from Dioxinones
Chen, Ming
Hartwig, John F.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (45) : 12172 - 12176
[10] Iridium-Catalyzed Enantioselective Allylic Substitution of Unstabilized Enolates Derived from α,β-Unsaturated Ketone
Chen, Ming
Hartwig, John F.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (33) : 8691 - 8695

← 1 2 3 4 5 6 7 8 9 10 →