Pd-catalyzed [3+2] cycloaddition of cyclic ketimines and trimethylenemethanes toward N-fused pyrrolidines bearing a quaternary carbon

被引：5

作者：

Choi, Seoung-Mi ^{[1
]}

Do Kim, Kyeong ^{[1
]}

Park, Jong-Un ^{[1
]}

Xuan, Zi ^{[1
]}

Kim, Ju Hyun ^{[1
]}

机构：

[1] Gyeongsang Natl Univ, Res Inst Nat Sci, Dept Chem BK21 Four, Jinju 52828, South Korea

来源：

RSC ADVANCES | 2021年 / 12卷 / 02期

基金：

新加坡国家研究基金会;

关键词：

BAYLIS-HILLMAN CARBONATES; ENANTIOSELECTIVE SYNTHESIS; NITROGEN-HETEROCYCLES; ASYMMETRIC-SYNTHESIS; CONSTRUCTION; CYCLOPROPANES; 1-AZADIENES; KETONES; ANNULATION; STRATEGY;

D O I：

10.1039/d1ra08579d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Pd-catalyzed [3 + 2] cycloaddition of N-sulfonyl cyclic ketimines and trimethylenemethanes (TMM) was developed that afforded N-fused pyrrolidines bearing a quaternary carbon. Under mild reaction conditions, structurally diverse N-sulfonyl cyclic imines, including sulfamate-fused aldimines, aryl- or styryl-substituted sulfamate-derived ketimines, and N-sulfonyl cyclic ketimines, were tolerated as reactants, affording N-fused pyrrolidines with high efficiency.

引用

页码：785 / 789

页数：5

共 41 条

[31] Base catalyzed abnormal [3+2]-cycloaddition reaction of isatin N,N′-cyclic azomethine imine with malononitrile via C-3 umpolung of oxindole [J].

Moghaddam, Firouz Matloubi ;

Aghamiri, Bagher ;

Eslami, Mohammad .

JOURNAL OF MOLECULAR STRUCTURE, 2024, 1299

[32] Pd(II)-Catalyzed [3+2] Annulation of N-Aryl-2-aminopyridines and Alkynes toward N-(2-Pyridyl)indoles [J].

Guo, Wenting ;

Hu, Weiming ;

Zhang, Xinyu ;

Huang, Jiali ;

Wang, Huiyan ;

Xia, Ming ;

Tao, Li .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (04)

[33] Asymmetric synthesis of 4-aryl-1,2,5-thiadiazolidin-3-one 1,1-dioxides via Pd-catalyzed hydrogenation of cyclic ketimines [J].

Zhu, Zhou-Hao ;

Chen, Meng-Lin ;

Jiang, Guo-Fang .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (06) :1325-1328

[34] Nickel(II)-catalyzed diastereoselective [3+2] cycloaddition of N-tosyl-aziridines and aldehydes via selective carbon-carbon bond cleavage [J].

Wu, Xingxing ;

Lia, Lei ;

Zhang, Junliang .

CHEMICAL COMMUNICATIONS, 2011, 47 (27) :7824-7826

[35] Copper-Catalyzed Ring-Opening (3+2) Annulation of Cyclopropenones with Ketoxime Acetates: Access to 1,2-Dihydro-pyrrol-3-ones Bearing a Quaternary Carbon Center [J].

Wang, Zhen-Hua ;

Yang, Ping ;

Zhang, Yan-Ping ;

You, Yong ;

Zhao, Jian-Qiang ;

Zhou, Ming-Qiang ;

Yuan, Wei-Cheng .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (18)

[36] Rhodium-catalyzed intermolecular [3+3] cycloaddition of vinyl aziridines with C,N-cyclic azomethine imines: stereospecific synthesis of chiral fused tricyclic 1,2,4-hexahydrotriazines [J].

Zhu, Chao-Ze ;

Feng, Jian-Jun ;

Zhang, Junliang .

CHEMICAL COMMUNICATIONS, 2017, 53 (34) :4688-4691

[37] Rhodium-Catalyzed Asymmetric (3+2+2) Annulation via N-H/C-H Dual Activation and Internal Alkyne Insertion toward N-Fused 5/7 Bicycles [J].

Yang, Chao ;

Shi, Lijun ;

Wang, Fang ;

Su, Yijin ;

Xia, Ji-Bao ;

Li, Fuwei .

ACS CATALYSIS, 2022, 12 (22) :14194-14208

[38] Copper-Catalyzed Diastereo- and Enantioselective Decarboxylative [3+2] Cyclization of Alkyne-Substituted Cyclic Carbamates with Azlactones: Access to γ-Butyrolactams Bearing Two Vicinal Tetrasubstituted Carbon Stereocenters [J].

Wang, Ting ;

You, Yong ;

Wang, Zhen-Hua ;

Zhao, Jian-Qiang ;

Zhang, Yan-Ping ;

Yin, Jun-Qing ;

Zhou, Ming-Qiang ;

Cui, Bao-Dong ;

Yuan, Wei-Cheng .

ORGANIC LETTERS, 2023, :1274-1279

[39] Asymmetric Rh(I)-Catalyzed Intramolecular [3+2] Cycloaddition of 1-Yne-vinylcyclopropanes for Bicyclo[3.3.0] Compounds with a Chiral Quaternary Carbon Stereocenter and Density Functional Theory Study of the Origins of Enantioselectivity [J].

Lin, Mu ;

Kang, Guan-Yu ;

Guo, Yi-An ;

Yu, Zhi-Xiang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) :398-405

[40] Pd-Catalyzed One-Pot Insertion Reaction of Cyclic C-Acylimines into Carbon-Carbon σ-Bonds for the Synthesis of Polyfunctional Indolin-3-ones from 2-Alkynyl Arylazides and Aryl Ketones [J].

Li, Ping ;

Yong, Wanxiong ;

Sheng, Rong ;

Rao, Weidong ;

Zhu, Xinbao ;

Zhang, Xiaoxiang .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (01) :201-207

← 1 2 3 4 5 →