Copper-Catalyzed Chemo- and Diastereoselective 1,3-Dipolar Cycloaddition of Carbonyl Ylide and Aldehyde-Tethered-Cyclohexadienone to Access Polycyclic Systems

被引：8

作者：

Peng, Shiyong ^{[1
]}

Zhang, Hong ^{[1
]}

Zhu, Yuqi ^{[1
]}

Zhou, Ting ^{[1
]}

He, Jieyin ^{[1
]}

Chen, Nuan ^{[1
]}

Lang, Ming ^{[1
]}

Li, Hongguang ^{[1
]}

Wang, Jian ^{[1
,2
]}

机构：

[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, Hangmen 529020, Peoples R China

[2] Tsinghua Univ, Key Lab Bioorgan Phosphorous Chem & Chem Biol, Sch Pharmaceut Sci, Minist Educ, Beijing 100084, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2021年 / 363卷 / 19期

关键词：

copper catalysis; 1,3-dipolar cycloaddition; carbonyl ylide; polycyclic structure; ORGANIC-SYNTHESIS; DIAZO-COMPOUNDS; TANDEM; CASCADE; STEREOCONTROL; CARBENOIDS; ALDIMINES;

D O I：

10.1002/adsc.202100648

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A copper-catalyzed tandem intermolecular ylide formation/intramolecular cycloaddition of diazo compounds and aldehyde-tethered-cyclohexadienones was reported, chemo- and diastereoselectively providing oxapolycyclic frameworks in moderate to excellent yields under mild conditions. This reaction creates two C-C bonds and one C-O bond with five stereocentres including two all-carbon quaternary centres. Moreover, the late-stage diversification of products can be realized via chemoselective substitutions.

引用

页码：4532 / 4537

页数：6

共 2 条

[1] Synthesis of 3-(1H-1,2,3-Triazol-1-yl)-2-(arylselanyl)pyridines by Copper-Catalyzed 1,3-Dipolar Cycloaddition of 2-(Arylselanyl)-3-azido-pyridines with Terminal Alkynes
Schumacher, Ricardo F.
Von Laer, Patrick B.
Betin, Eduardo S.
Cargnelutti, Roberta
Perin, Gelson
Alves, Diego
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2015, 26 (11) : 2298 - 2306
[2] Synthesis of novel spirocyclic 2-oxindole tethered to 2′-(3-(furan-2-yl)-1H-pyrazole-4-carbonyl)-hexahydropyrrolizine via 1,3-dipolar cycloaddition of the chalcone with azomethine ylide: Reaction of pyrazolyl-enaminone towards some heteroaromatic amines
Saleh, Fatma M.
Hassaneen, Hamdi M.
Abdelhamid, Ismail A.
Teleb, Mohamed A. Mohamed
TETRAHEDRON LETTERS, 2024, 137

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