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

[1] Iridium-Catalyzed Enantioselective and Chemodivergent Allenylic Alkylation of Vinyl Azides for the Synthesis of α-Allenylic Amides and Ketones [J].

Chakrabarty, Aditya ;

Mukherjee, Santanu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (12)

[2] Iridium-Catalyzed Enantioselective α-Allylic Alkylation of Amides Using Vinyl Azide as Amide Enolate Surrogate [J].

Chakrabarty, Aditya ;

Mukherjee, Santanu .

ORGANIC LETTERS, 2020, 22 (19) :7752-7756

[3] Chiral oxamide-phosphine-palladium catalyzed highly asymmetric allylic amination: carbonyl assistance for high regio- and enantiocontrols [J].

Chen, Jun-Bo ;

Peng, Cheng ;

Zhou, Sheng-Suo ;

Wang, Yong ;

Wang, Zheng ;

Wang, Xing-Wang .

ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (15) :3976-3989

[4] Recent advances of versatile reagents as controllable building blocks in organic synthesis [J].

Chen, Shaomin ;

Vaccaro, Luigi ;

Gu, Yanlong .

CHINESE CHEMICAL LETTERS, 2024, 35 (02)

[5] Iridium-Catalyzed Asymmetric Allylic Substitution Reactions [J].

Cheng, Qiang ;

Tu, Hang-Fei ;

Zheng, Chao ;

Qu, Jian-Ping ;

Helmchen, Guenter ;

You, Shu-Li .

CHEMICAL REVIEWS, 2019, 119 (03) :1855-1969

[6] Spirocyclic Motifs in Natural Products [J].

Chupakhin, Evgeny ;

Babich, Olga ;

Prosekov, Alexander ;

Asyakina, Lyudmila ;

Krasavin, Mikhail .

MOLECULES, 2019, 24 (22)

[7] Isoxazol-5-ones as Strategic Building Blocks in Organic Synthesis [J].

da Silva, Amanda F. ;

Fernandes, Alessandra A. G. ;

Thurow, Samuel ;

Stivanin, Mateus L. ;

Jurberg, Igor D. .

SYNTHESIS-STUTTGART, 2018, 50 (13) :2473-2489

[8] α-Substituted vinyl azides: an emerging functionalized alkene [J].

Fu, Junkai ;

Zanoni, Giuseppe ;

Anderson, Edward A. ;

Bi, Xihe .

CHEMICAL SOCIETY REVIEWS, 2017, 46 (23) :7208-7228

[9] Vinyl azides in organic synthesis: an overview [J].

Gholami, Fateme ;

Yousefnejad, Faeze ;

Larijani, Bagher ;

Mahdavi, Mohammad .

RSC ADVANCES, 2023, 13 (02) :990-1018

[10] Synthesis, biological evaluation, and molecular modelling studies of potent human neutrophil elastase (HNE) inhibitors [J].

Giovannoni, Maria Paola ;

Schepetkin, Igor A. ;

Quinn, Mark T. ;

Cantini, Niccolo ;

Crocetti, Letizia ;

Guerrini, Gabriella ;

Iacovone, Antonella ;

Paoli, Paola ;

Rossi, Patrizia ;

Bartolucci, Gianluca ;

Menicatti, Marta ;

Vergelli, Claudia .

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2018, 33 (01) :1108-1124

← 1 2 3 4 5 6 7 →