The (3+2)- and formal (3+3)-cycloadditions of N-vinylpyrroles with cyclic nitrones and C,N-cyclic azomethine imines

被引：10

作者：

Afanaseva, Kseniia K. ^{[1
]}

Efremova, Mariia M. ^{[1
]}

Kuznetsova, Svetlana, V ^{[2
]}

Ivanov, Andrey, V ^{[2
]}

Starova, Galina L. ^{[1
]}

Molchanov, Alexander P. ^{[1
]}

机构：

[1] St Petersburg State Univ, Univ Skaya Nab 7-9, St Petersburg 199034, Russia

[2] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, 1 Favorsky Str, Irkutsk 664033, Russia

来源：

TETRAHEDRON | 2018年 / 74卷 / 39期

关键词：

Cycloaddition; N-Vinylpyrroles; Lewis acids; Nitrones; Azomethine imines; ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION; DONOR-ACCEPTOR CYCLOPROPANES; STEREOSELECTIVE CYCLOADDITION; 1-(1H-INDOL-3-YL)ETHANAMINE DERIVATIVES; HIGHLY EFFICIENT; NITRILE OXIDES; EASY ACCESS; INDOLES; YLIDES; PYRROLES;

D O I：

10.1016/j.tet.2018.07.040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of Lewis acids changes the path of the reaction of N-vinylpyrroles with 3,4-dihydroisoquinoline-N-oxides: formal (3 + 3)-cycloaddition proceeds instead of (3 + 2)-cycloaddition. In the case of benzoyl(3,4-dihydroisoquinolin-2-ium-2-yl)amides, reaction path does not change in the same conditions, but changing of the diastereoselectivity occurs and other diastereomer of (3 + 2)-cycloaddition became predominant. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：5665 / 5673

页数：9

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