Palladium-Catalyzed Asymmetric Decarboxylation of 5-Vinyloxazolidine-2,4-Diones Triggering the Dearomatization of Electron-Deficient Indoles for the Synthesis of Chiral Highly Functionalized Pyrroloindolines

被引：12

作者：

Dou, Pei-Hao ^{[1
,2
,3
]}

Fu, Xiao-Hui ^{[1
,2
,3
]}

Chen, Yan ^{[1
,2
,3
]}

Ge, Zhen-Zhen ^{[2
,3
]}

Zhou, Ming-Qiang ^{[2
,3
]}

Wang, Zhen-Hua ^{[1
]}

You, Yong ^{[1
]}

Yang, Lei ^{[1
]}

Zhang, Yan-Ping ^{[1
]}

Zhao, Jian-Qiang ^{[1
]}

Yuan, Wei-Cheng ^{[1
,2
,3
]}

机构：

[1] Chengdu Univ, Inst Adv Study, Innovat Res Ctr Chiral Drugs, Chengdu 610106, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Peoples R China

[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 15期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE SYNTHESIS; CASCADE DEAROMATIZATION; CONSTRUCTION; CYCLOADDITION; DERIVATIVES; ACCESS; FUROINDOLINES; ANNULATION; CATIONS;

D O I：

10.1021/acs.orglett.4c01003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalyst system consisting of a chiral phosphoramidite ligand and Pd-2(dba)(3)<middle dot>CHCl3 causes the decarboxylation of 5-vinyloxazolidine-2,4-diones to generate amide-containing aza-pi-allylpalladium 1,3-dipole intermediates, which are capable of triggering the dearomatization of 3-nitroindoles for diastereo- and enantioselective [3+2] cycloaddition, leading to the formation of a series of highly functionalized pyrroloindolines containing three contiguous stereogenic centers with excellent results (up to 99% yield, 88:12 dr, and 96% ee).

引用

页码：3310 / 3315

页数：6

共 52 条

[51] Enantioselective Copper-Catalyzed Construction of Aryl Pyrroloindolines via an Arylation-Cyclization Cascade [J].

Zhu, Shaolin ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (26) :10815-10818

[52] Transition-Metal-Catalyzed Asymmetric Allylic Dearomatization Reactions [J].

Zhuo, Chun-Xiang ;

Zheng, Chao ;

You, Shu-Li .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (08) :2558-2573

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