Iridium-catalyzed highly enantioselective and chemodivergent coupling reaction of vinyl azides and vinyl benzoxazinones

被引：2

作者：

Gan, Deli ^{[1
]}

Zhao, Sumei ^{[1
]}

Yang, Min ^{[1
]}

Xu, Minghui ^{[1
]}

Chen, Bin ^{[1
]}

Ni, Hai-Liang ^{[1
]}

Yu, Wenhao ^{[1
]}

Wang, Bi-Qin ^{[1
]}

Hu, Ping ^{[1
]}

Cao, Peng ^{[1
]}

机构：

[1] Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 610068, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2025年 / 12卷 / 02期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC ALLYLIC ALKYLATION; PALLADIUM; CYCLOADDITIONS; CYCLOPROPANOLS; CONSTRUCTION; ALLYLATION;

D O I：

10.1039/d4qo01862a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first iridium-catalyzed enantioselective coupling reaction of vinyl azides and vinyl benzoxazinones is presented. Vinyl azides underwent a tandem allylic alkylation/interrupted Schmidt rearrangement process to produce enantioenriched 3,4-dihydroquinolin-2(1H)-imines, a new class of N-heterocycles. In the presence of CH3CO2H, a conventional asymmetric allylic substitution occurred to provide access to nonracemic allylic amides. The synthetic transformations of the product were carried out to construct chiral amines, amides and N-hetero polycycles.

引用

页码：607 / 613

页数：7

共 69 条

[41] Iridium and a Bronsted acid cooperatively catalyzed chemodivergent and stereoselective reactions of vinyl benzoxazinones with azlactones [J].

Sun, Meng ;

Wan, Xiao ;

Zhou, Si-Jia ;

Mei, Guang-Jian ;

Shi, Feng .

CHEMICAL COMMUNICATIONS, 2019, 55 (09) :1283-1286

[42] Highly selective allylic alkylation with a carbon nucleophile at the more substituted allylic terminus catalyzed by an iridium complex: An efficient method for constructing quaternary carbon centers [J].

Takeuchi, R ;

Kashio, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (03) :263-265

[43] Divergent synthesis of chiral cyclic azides via asymmetric cycloaddition reactions of vinyl azides [J].

Thirupathi, Nuligonda ;

Wei, Fang ;

Tung, Chen-Ho ;

Xu, Zhenghu .

NATURE COMMUNICATIONS, 2019, 10

[44] Chiral Cyclic Ligand-Enabled Iridium-Catalyzed Asymmetric Arylation of Unactivated Racemic Allylic Alcohols with Anilines [J].

Tian, Hua ;

Zhang, Pengxiang ;

Peng, Fei ;

Yang, Haijun ;

Fu, Hua .

ORGANIC LETTERS, 2017, 19 (14) :3775-3778

[45] Recent Advances in Metal-Catalyzed Decarboxylative Reactions of Vinyl Benzoxazinanones [J].

Tian, Ye ;

Duan, Meibo ;

Liu, Jialu ;

Fu, Siyu ;

Dong, Kuan ;

Yue, Hao ;

Hou, Yunlei ;

Zhao, Yanfang .

ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (19) :4461-4474

[46] Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: A working model [J].

Trost, Barry M. ;

Machacek, Michelle R. ;

Aponick, Aaron .

ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (10) :747-760

[47] Annulative Allylic Alkylation Reactions between Dual Electrophiles and Dual Nucleophiles: Applications in Complex Molecule Synthesis [J].

Trost, Barry M. ;

Kalnmals, Christopher A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (09) :1906-1921

[48] Asymmetric transition metal-catalyzed allylic alkylations [J].

Trost, BM ;

VanVranken, DL .

CHEMICAL REVIEWS, 1996, 96 (01) :395-422

[49] Asymmetric allylic alkylation, an enabling methodology [J].

Trost, BM .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18) :5813-5837

[50] Asymmetric transition-metal-catalyzed allylic alkylations: Applications in total synthesis [J].

Trost, BM ;

Crawley, ML .

CHEMICAL REVIEWS, 2003, 103 (08) :2921-2943

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