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

被引：9
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
收藏
页码：5665 / 5673
页数：9
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