Microwave-assisted [3+2] cycloadditions of azomethine ylides

被引：52

作者：

Bashiardes, G ^{[1
]}

Safir, I ^{[1
]}

Mohamed, AS ^{[1
]}

Barbot, F ^{[1
]}

Laduranty, J ^{[1
]}

机构：

[1] Univ Poitiers, SFA UMR 6514, Dept Chim Methodol & Synth Biomol, F-86022 Poitiers, France

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 25期

关键词：

D O I：

10.1021/ol0361195

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The microwave-assisted intramolecular [3 + 2] cycloaddition reaction of azomethine ylides to activated and nonactivated alkenes and alkynes is described. The procedure allows the synthesis of pyrrolidines and pyrrole products in good to excellent overall yields in short reaction times. It appears from parallel comparative studies that the microwave procedure favors the reaction times and overall purity of the crude reaction mixture. The reactions can also be performed in the absence of solvent.

引用

页码：4915 / 4918

页数：4

共 50 条

[31] INTRAMOLECULAR CYCLOADDITIONS WITH AZOMETHINE YLIDES FOR THE SYNTHESIS OF METACYCLOPHANES
EBERBACH, W
FRITZ, H
HEINZE, I
VONLAER, P
LINK, P
TETRAHEDRON LETTERS, 1986, 27 (34) : 4003 - 4006
[32] CuI-Catalyzed Asymmetric [3+2] Cycloaddition of Azomethine Ylides with Cyclobutenones
Corpas, Javier
Ponce, Alberto
Adrio, Javier
Carretero, Juan C.
ORGANIC LETTERS, 2018, 20 (11) : 3179 - 3182
[33] Enantioselective ag(i)-catalyzed [3+2] cycloaddition of azomethine ylides.
Zhang, XM
Raghunath, M
Longmire, J
Wang, B
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U208 - U208
[34] Synthesis of ferrocenyl monospirooxindolopyrrolidines-a facile [3+2]-cycloaddition of azomethine ylides
Babu, A. R. Suresh
Raghunathan, R.
TETRAHEDRON LETTERS, 2008, 49 (29-30) : 4487 - 4490
[35] A NEW ACCESS TO PHOSPHAINDOLIZINES BY [3+2] CYCLOADDITION OF AZOMETHINE YLIDES ONTO PHOSPHAALKYNES
BERGSTRASSER, U
HOFFMANN, A
REGITZ, M
TETRAHEDRON LETTERS, 1992, 33 (08) : 1049 - 1052
[36] Catalytic Enantioselective [3+2] Cycloaddition of N-Metalated Azomethine Ylides
Kumar, Sundaravel Vivek
Guiry, Patrick J.
CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (28)
[37] Bifunctional AgOAc-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides
Zeng, W
Zhou, YG
ORGANIC LETTERS, 2005, 7 (22) : 5055 - 5058
[38] Microwave-assisted synthesis of peptidyl phosphorus ylides
Katritzky, AR
Vincek, AS
Suzuki, K
ARKIVOC, 2005, : 116 - 126
[39] Highly Enantioselective Catalytic [6+3] Cycloadditions of Azomethine Ylides
Potowski, Marco
Bauer, Jonathan O.
Strohmann, Carsten
Antonchick, Andrey P.
Waldmann, Herbert
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (38) : 9512 - 9516
[40] Microwave-assisted multicomponent diastereoselective 1,3-dipolar cycloaddition of ethyl glyoxylate derived azomethine ylides
Mancebo-Aracil, Juan
Najera, Carmen
Sansano, Jose M.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (04) : 662 - 675

← 1 2 3 4 5 →