Lewis acid-catalyzed formal [3+2] cycloadditions of N-tosyl aziridines with electron-rich alkenes via selective carbon-carbon bond cleavage

被引：54

作者：

Li, Lei ^{[1
]}

Wu, Xingxing ^{[1
]}

Zhang, Junliang ^{[1
]}

机构：

[1] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 17期

基金：

中国国家自然科学基金;

关键词：

RING-OPENING REACTION; AZOMETHINE YLIDES; C-C; DIPOLAR CYCLOADDITION; MESO-AZIRIDINES; COMPLEXES; NITRONES; DESYMMETRIZATION; EPOXIDES; TRIFLATE;

D O I：

10.1039/c1cc10926j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel, mild, robust catalyst Y(OTf)(3) for C-C bond heterolysis of N-tosyl aziridines was developed and the resulting metallo-azomethine ylides may readily undergo [3+2] dipolar cycloaddition with an electron-rich olefin via a stepwise reaction pathway with high regio- and diastereoselectivity leading to substituted pyrrolidines.

引用

页码：5049 / 5051

页数：3

共 22 条

[1] Nickel(II)-catalyzed diastereoselective [3+2] cycloaddition of N-tosyl-aziridines and aldehydes via selective carbon-carbon bond cleavage
Wu, Xingxing
Lia, Lei
Zhang, Junliang
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (27) : 7824 - 7826
[2] Lewis acid-catalyzed [3+3] cycloadditions of donor-acceptor aziridines with N,N-dialkyl-3-vinylanilines via carbon-carbon bond cleavage
Lee, Sang Gyu
Kim, Sung-Gon
[J]. TETRAHEDRON, 2018, 74 (27) : 3671 - 3678
[3] Lewis Acid-catalyzed [3+2]Cycloaddition of Alkynes with N-Tosylaziridines via Carbon-Carbon Bond Cleavage: Synthesis of Highly Substituted 3-Pyrrolines
Li, Lei
Zhang, Junliang
[J]. ORGANIC LETTERS, 2011, 13 (22) : 5940 - 5943
[4] Highly regioselective Lewis acid-catalyzed [3+2] cycloaddition of alkynes with donor-acceptor oxiranes by selective carbon-carbon bond cleavage of epoxides
Liu, Renrong
Zhang, Mei
Zhang, Junliang
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (48) : 12870 - 12872
[5] Lewis acid-catalyzed [3p3] cycloadditions of donor-acceptor aziridines with N,N-dialkyl-3-vinylanilines via carbon-carbon bond cleavage (vol 74, pg 3671, 2018)
Lee, Sang Gyu
Kim, Sung-Gon
[J]. TETRAHEDRON, 2019, 75 (02) : 324 - 326
[6] Asymmetric [3+2] cycloaddition of donor-acceptor aziridines with aldehydes via carbon-carbon bond cleavage
Liao, Yuting
Liu, Xiaohua
Zhang, Yu
Xu, Yali
Xia, Yong
Lin, Lili
Feng, Xiaoming
[J]. CHEMICAL SCIENCE, 2016, 7 (06) : 3775 - 3779
[7] Formal [3+2] Cycloaddition Reactions of Electron-Rich Aryl Epoxides with Alkenes under Lewis Acid Catalysis Affording Tetrasubstituted Tetrahydrofurans
Macias-Villamizar, Victor E.
Cuca-Suarez, Luis
Rodriguez, Santiago
Gonzalez, Florenci, V
[J]. MOLECULES, 2020, 25 (03):
[8] Lewis Acid Catalyzed SN2-Type Ring Opening of N-Activated Aziridines with Electron-Rich Arenes/Heteroarenes
Ghorai, Manas K.
Tiwari, Deo Prakash
Jain, Nikita
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14): : 7121 - 7130
[9] Ru(II)-Catalyzed Deoxygenative Formal [3+1+2] Benzannulation of Allyl Alcohols and Acetylenediesters via C-H Activation and Selective Carbon-Carbon Triple Bond Cleavage
Dethe, Dattatraya H.
Uike, Amar
Beeralingappa, Nagabhushana C.
[J]. ORGANIC LETTERS, 2024, 26 (10) : 2013 - 2017
[10] A Unified Approach for Divergent Synthesis of Heterocycles via TMSOTf-Catalyzed Formal [3+2] Cycloaddition of Electron-Rich Alkynes
Chen, Ping
Cao, Wei
Li, Xiangqian
Shi, Dayong
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (20) : 4789 - 4794

← 1 2 3 →