Relay Catalysis of Rh (II) and Cobaloxime: Stereoselective Synthesis of Spiroindanones from N-Sulfonyl-1,2,3-triazoles

被引:26
作者
Liu, Zhao [1 ]
Du, Qiuchen [1 ]
Zhai, Hongbin [1 ]
Li, Yun [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
DIVERGENT SYNTHESIS; SUBSTITUTED INDANONES; 3+2 CYCLOADDITION; ACCESS; 1-SULFONYL-1,2,3-TRIAZOLES; TRANSANNULATION; 1,2,3-TRIAZOLES; TRANSFORMATIONS; CONSTRUCTION; FRAMEWORK;
D O I
10.1021/acs.orglett.8b03275
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel relay Rh (II)/cobaloxime (III) dual catalysis strategy has been developed for the stereoselective synthesis of indolyl spiroindanones from readily accessible N-sulfony1-1,2,3-triazoles. This binary-catalyst system enables an aza-vinyl carbene initiated Pictet-Spengler-type cyclization and sequential cobaloxime promoted intramolecular Mannich-type reaction cascade. The easily accessible reagents, high diastereoselectivity, and operational simplicity make this reaction a method of choice for the preparation of functionalized spiroindanones, which are difficult to access by other classic reactions in one step.
引用
收藏
页码:7514 / 7517
页数:4
相关论文
共 49 条
[11]   Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes [J].
Guarnieri-Ibanez, Alejandro ;
Medina, Florian ;
Besnard, Celine ;
Kidd, Sarah L. ;
Spring, David R. ;
Lacour, Jerome .
CHEMICAL SCIENCE, 2017, 8 (08) :5713-5720
[12]  
HANAOKA M, 1985, CHEM PHARM BULL, V33, P2621
[13]   Rhodium-Catalyzed Synthesis of 4-Bromo-1,2-dihydroisoquinolines: Access to Bromonium Ylides by the Intramolecular Reaction of a Benzyl Bromide and an -Imino Carbene [J].
He, Jun ;
Shi, Yinping ;
Cheng, Wanli ;
Man, Zengming ;
Yang, Dongdong ;
Li, Chuan-Ying .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (14) :4557-4561
[14]   Cobaloxime-catalyzed hydration of terminal alkynes without acidic promoters [J].
Hou, Shengtai ;
Yang, Hongjian ;
Cheng, Bin ;
Zhai, Hongbin ;
Li, Yun .
CHEMICAL COMMUNICATIONS, 2017, 53 (51) :6926-6929
[15]   C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA OF SPIROBENZYLISOQUINOLINE ALKALOIDS AND RELATED MODEL COMPOUNDS [J].
HUGHES, DW ;
NALLIAH, BC ;
HOLLAND, HL ;
MACLEAN, DB .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (18) :3304-3311
[16]   Recent Advances in the Synthesis of Heterocycles and Related Substances Based on α-Imino Rhodium Carbene Complexes Derived from N-Sulfonyl-1,2,3-triazoles [J].
Jiang, Yu ;
Sun, Run ;
Tang, Xiang-Ying ;
Shi, Min .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (50) :17910-17924
[17]   Multicomponent [5+2] Cycloaddition Reaction for the Synthesis of 1,4-Diazepines: Isolation and Reactivity of Azomethine Ylides [J].
Lee, Dong Jin ;
Han, Hong Sik ;
Shin, Jinhwan ;
Yoo, Eun Jeong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (33) :11606-11609
[18]   Synthesis of 6-Substituted Piperidin-3-ones via Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles with Electron-Rich Aromatic Nucleophiles [J].
Li, Yang ;
Zhang, Ran ;
Ali, Arshad ;
Zhang, Jing ;
Bi, Xihe ;
Fu, Junkai .
ORGANIC LETTERS, 2017, 19 (12) :3087-3090
[19]   The Expanding Utility of Rhodium-Iminocarbenes: Recent Advances in the Synthesis of Natural Products and Related Scaffolds [J].
Li, Yun ;
Yang, Hongjian ;
Zhai, Hongbin .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (49) :12757-12766
[20]   Rh-Catalyzed [3+2] Cycloaddition of 1-Sulfonyl-1,2,3-triazoles: Access to the Framework of Aspidosperma and Kopsia Indole Alkaloids [J].
Li, Yun ;
Zhang, Qingyu ;
Du, Qiucheng ;
Zhai, Hongbin .
ORGANIC LETTERS, 2016, 18 (16) :4076-4079