Accessing polysubstituted oxazolidines, pyrrolidines and imidazolidines by regioselective [3+2] annulations of ketenimines with donor-acceptor oxiranes and aziridines

被引：27

作者：

Alajarin, Mateo ^{[1
]}

Banon, Daniel ^{[1
]}

Egea, Adrian ^{[1
]}

Marin-Luna, Marta ^{[2
]}

Orenes, Raul-Angel ^{[3
]}

Vidal, Angel ^{[1
]}

机构：

[1] Univ Murcia, Dept Quim Organ, Fac Quim, Reg Campus Int Excellence,Campus Mare Nostrum, E-30100 Murcia, Spain

[2] Univ Vigo, Dept Quim Organ, Vigo 36310, Spain

[3] Univ Murcia, Serv Univ Instrumentac Cient, Reg Campus Int Excellence,Campus Mare Nostrum, Murcia 30100, Spain

来源：

ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 13期

关键词：

CARBON BOND-CLEAVAGE; INTRAMOLECULAR 2+2 CYCLOADDITIONS; HIGHLY EFFICIENT SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; AZOMETHINE YLIDES; 2,3-DISUBSTITUTED INDOLES; STEREOSELECTIVE-SYNTHESIS; CATALYZED ANNULATION; BENZYLIC RADICALS; N-TOSYLAZIRIDINES;

D O I：

10.1039/c8qo00255j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient [3 + 2] annulations of N-aryl-C, C-diphenyl ketenimines with metallo-carbonyl and metallo-azomethine ylides, generated via the respective Yb(OTf)(3) and Y(OTf)(3) promoted carbon-carbon bond heterolysis of donor-acceptor oxiranes and aziridines, have been accomplished. These reactions proceeded under mild conditions and supplied a general methodology for the regioselective construction of structurally complex oxazolidines and pyrrolidines. Moreover, heating neat mixtures of N-aryl-C, C-diphenyl ketenimines and diethyl aziridine-2,3-dicarboxylates led to imidazolidine derivatives. A computational study concluded in stepwise mechanisms for these [3 + 2] annulations, also shedding light on their regioselectivity, concerning which of the two cumulated double bonds of the ketenimine becomes involved in the reaction with the ylide.

引用

页码：2020 / 2029

页数：10

共 103 条

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