Synthesis of Bisspiro(oxindole)s by DMAP-Catalyzed [3+2] Annulation of Isatin-Derived Morita-Baylis-Hillman Carbonates

被引：4

作者：

Wang, Xiaohao ^{[1
]}

Wei, Xingfu ^{[1
]}

Xu, Yongqiang ^{[1
]}

Qu, Jingping ^{[1
]}

Wang, Baomin ^{[1
]}

机构：

[1] Dalian Univ Technol, Sch Chem Engn, Dept Pharmaceut Engn, State Key Lab Fine Chem, 2 Linggong Rd, Dalian 116024, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 28期

关键词：

3+2] annulation; Lewis base catalysis; Morita-Baylis-Hillman carbonates; p-quinone methides; Spirooxindoles;

D O I：

10.1002/ejoc.202400396

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward [3+2] annulation method for synthesizing bisspiro(oxindole) derivatives has been developed by using isatin-derived Morita-Baylis-Hillman carbonates and p-quinone methides (p-QMs) with 4-dimethylaminopyridine (DMAP) as the catalyst. The optimized protocol in dichloromethane (DCM) solvent achieves good yields (up to 87 %) and diastereoselectivity (>20 : 1). The versatility of the method is shown through the synthesis of various derivatives, including chiral variants with up to 82 % ee. The intermediates were captured by HRMS, and a plausible reaction pathway was proposed.

引用

页数：5

共 39 条

[1] A Proline-Squaraine Ligand Framework (Pro-SqEB) for Stereoselective Rhodium(II)-Catalyzed Cyclopropanations [J].

Bacher, Emily P. ;

Twiringiyimana, Raissa ;

Rodriguez, Kevin X. ;

Wilson, Renita A. ;

Bodnar, Alexandra K. ;

O'Connell, Ryan ;

Toni, Tiffany A. ;

Eckert, Kaitlyn E. ;

Wiest, Olaf ;

Ashfeld, Brandon L. .

ORGANIC LETTERS, 2023, 25 (45) :8156-8161

[2] Cooperative Tertiary Amine/Palladium-Catalyzed Sequential [4+3] Cyclization/[1,3]-Rearrangement for Stereoselective Synthesis of Spiro [Methylenecyclopentane-1,3′-oxindolines] [J].

Chen, Yue-You ;

Zhou, Chen-Dong ;

Li, Xing-Tong ;

Yang, Ting-You ;

Han, Wen-Yong ;

Wan, Nan-Wei ;

Chen, Yong-Zheng ;

Cui, Bao-Dong .

JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (01) :371-383

[3] Transformations of Modified Morita-Baylis-Hillman Adducts from Isatins Catalyzed by Lewis Bases [J].

Chen, Zhi-Chao ;

Chen, Zhi ;

Du, Wei ;

Chen, Ying-Chun .

CHEMICAL RECORD, 2020, 20 (06) :541-555

[4] Asymmetric Catalytic 1,6-Conjugate Addition/Aromatization of para-Quinone Methides: Enantioselective Introduction of Functionalized Diarylmethine Stereogenic Centers [J].

Chu, Wen-Dao ;

Zhang, Le-Fen ;

Bao, Xu ;

Zhao, Xian-He ;

Zeng, Chao ;

Du, Ji-Yuan ;

Zhang, Guo-Biao ;

Wang, Fang-Xin ;

Ma, Xiao-Yan ;

Fan, Chun-An .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) :9229-9233

[5] Palladium-Catalyzed Annulative Coupling of Spirovinylcyclopropyl Oxindoles with p-Quinone Methides [J].

Debnath, Bijoy ;

Sarkar, Tanumay ;

Karjee, Pallab ;

Purkayastha, Siddhartha K. ;

Guha, Ankur K. ;

Punniyamurthy, Tharmalingam .

JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (14) :9704-9719

[6] Tertiary Amine-Catalyzed Difluoromethylthiolation of Morita-Baylis-Hillman Carbonates of Isatins with Zard's Trifluoromethylthiolation Reagent [J].

Fan, Xing ;

Yang, Haibin ;

Shi, Min .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (01) :49-57

[7] 4-Dimethylaminopyridine-catalyzed [3+3] spiroannulation reactions of isatin-derived Morita-Baylis-Hillman carbonates with indoline-2-thiones [J].

Geng, Congcong ;

Wei, Xingfu ;

Xu, Yongqiang ;

Liu, Jianhui ;

Peng, Lizeng ;

Wang, Baomin .

TETRAHEDRON LETTERS, 2022, 102

[8] Enantioselective Synthesis of Bispiro[indanedione-oxindole-cyclopropane]s through Organocatalytic [2+1] Cycloaddition [J].

Hao, Zhi-Feng ;

Zhu, Shi-Jie ;

Hao, Yong-Jia ;

Zhang, Wen-Hui ;

Zhou, Ying ;

Tian, You-Ping ;

Lei, Chuan-Wen .

JOURNAL OF ORGANIC CHEMISTRY, 2022, 88 (12) :7641-7650

[9] Asymmetric [3+2] Annulations to Construct 1,2-Bispirooxindoles Incorporating a Dihydropyrrolidine Motif [J].

He, Qing ;

Du, Wei ;

Chen, Ying-Chun .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (21) :3782-3791

[10] Catalytic asymmetric construction of dispirotriheterocyclic structures through [3+2] cycloadditions of 4-amino pyrazolone-based azomethine ylides [J].

Huang, Yue ;

Bao, Xiaoze ;

Wei, Xingfu ;

Zhang, Jianfang ;

Nawaz, Shah ;

Qu, Jingping ;

Wang, Baomin .

NEW JOURNAL OF CHEMISTRY, 2022, 46 (29) :14155-14158

← 1 2 3 4 →