Rhodium(II)-Catalyzed Intramolecular Cycloisomerizations of Methylenecyclopropanes with N-Sulfonyl 1,2,3-Triazoles

被引：120

作者：

Chen, Kai ^{[1
,2
]}

Zhu, Zi-Zhong ^{[1
,2
]}

Zhang, Yong-Sheng ^{[3
]}

Tang, Xiang-Ying ^{[3
]}

Shi, Min ^{[1
,2
,3
]}

机构：

[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 26期

基金：

中国国家自然科学基金;

关键词：

carbenes; isomerization; nitrogen heterocycles; rhodium; small ring systems; UNIQUE TETRASUBSTITUTED ALKENE; MGI2-MEDIATED RING EXPANSIONS; RH-CATALYZED TRANSANNULATION; TETHERED ALKYLIDENECYCLOPROPANES; CYCLOBUTANE DERIVATIVES; ANALGESIC ACTIVITY; BICYCLIC HOMOLOGS; TERMINAL ALKYNES; BOND-CLEAVAGE; REACTIVITY;

D O I：

10.1002/anie.201402803

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel rhodium(II)-catalyzed tandem cycloisomerization of methylenecyclopropanes (MCPs) with N-sulfonyl 1,2,3-triazoles is disclosed. The reaction produces a series of highly functionalized polycyclic N heterocycles via a rhodium imino carbene intermediate. A distinct feature of this divergent synthesis is that different types of substrates control the reaction pathways. Moreover, several interesting transformations of these products to construct diazabicyclo[3.2.1]octane derivatives are also reported.

引用

页码：6645 / 6649

页数：5

共 50 条

[1] Rhodium-catalyzed enantioselective cyclopropanation of olefins with N-sulfonyl 1,2,3-triazoles
Chuprakov, Stepan
Kwok, Sen Wai
Zhang, Li
Lercher, Lukas
Fokin, Valery V.
Journal of the American Chemical Society, 2009, 131 (50): : 18034 - 18035
[2] Rhodium-Catalyzed Enantioselective Cyclopropanation of Olefins with N-Sulfonyl 1,2,3-Triazoles
Chuprakov, Stepan
Kwok, Sen Wai
Zhang, Li
Lercher, Lukas
Fokin, Valery V.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (50) : 18034 - +
[3] Rhodium(II)-Catalyzed Denitrogenative Transformations of N-Sulfonyl-1,2,3-Triazoles
Doraghi, Fatemeh
Morshedsolouk, Mohammad Hossein
Ghofrani, Samaneh
Larijani, Bagher
Mahdavi, Mohammad
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (02)
[4] Rh(II)-catalyzed intramolecular annulation of N-sulfonyl 1,2,3-triazoles with indole derivatives: a new method for synthesis pyranoindoles
Xie, Hui
Yang, Jian-Xin
Bora, Pranjal Protim
Kang, Qiang
TETRAHEDRON, 2016, 72 (22) : 3014 - 3021
[5] Synthesis of Pyrazines from Rhodium-Catalyzed Reaction of 2H-Azirines with N-Sulfonyl 1,2,3-Triazoles
Ryu, Taekyu
Baek, Yonghyeon
Lee, Phil Ho
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (04): : 2376 - 2383
[6] Rhodium-Catalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles with Carboxylic Esters
Kaieda, Yuya
Yamamoto, Kosuke
Kuriyama, Masami
Onomura, Osamu
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (17) : 3081 - 3087
[7] Rhodium(II)-catalyzed intramolecular annulation of 1-sulfonyl-1,2,3-triazoles with indoles: facile synthesis of functionalized tetrahydro-β-carbolines
Shang, Hai
Tian, Yu
Luo, Jun
Li, Lingyu
Tang, Yefeng
Zou, Zhongmei
RSC ADVANCES, 2016, 6 (37): : 30835 - 30839
[8] Rh(II)-catalyzed intramolecular dearomatizing annulation of N-sulfonyl-1,2,3-triazoles: synthesis of polycyclic spiroindolines
Bora, Pranjal Protim
Luo, Zeng-Liang
Chen, Li
Kang, Qiang
TETRAHEDRON, 2016, 72 (11) : 1467 - 1471
[9] Rhodium(II)-Catalyzed and Thermally Induced Intramolecular Migration of N-Sulfonyl-1,2,3-triazoles: New Approaches to 1,2-Dihydroisoquinolines and 1-Indanones
Sun, Run
Jiang, Yu
Tang, Xiang-Ying
Shi, Min
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (16) : 5727 - 5733
[10] Rhodium(II)-Catalysed Skeletal Rearrangement of Ether Tethered N-Sulfonyl 1,2,3-Triazoles: a Rapid Approach to 2-Aminoindanone and Dihydroisoquinoline Derivatives
Yu, Yinghua
Zhu, Lei
Liao, Yun
Mao, Zhifeng
Huang, Xueliang
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (07) : 1059 - 1064

← 1 2 3 4 5 →