Diastereoselective Palladium-Catalyzed (3+2)-Cycloadditions from Cyclic Imines and Vinyl Aziridines

被引：55

作者：

Spielmann, Kim ^{[1
]}

van der Lee, Arie ^{[2
]}

de Figueiredo, Renata Marcia ^{[1
]}

Campagne, Jean-Marc ^{[1
]}

机构：

[1] Univ Montpellier, CNRS, ENSCM Ecole Natl Super Chim, ICGM,UMR 5253, 8 Rue Ecole Normale, F-34296 Montpellier 5, France

[2] Univ Montpellier, CNRS, UMR 5632, Xray Struct Anal,IEM, Pl Eugene Bataillon, F-34095 Montpellier 5, France

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 05期

关键词：

DEAROMATIVE 3+2 CYCLOADDITION; RING-OPENING CYCLIZATION; ASYMMETRIC CONSTRUCTION; HETEROCYCLES; IMIDAZOLIDINES; 3-NITROINDOLES; TRANSFORMATION; ALKYLATION; ACCESS;

D O I：

10.1021/acs.orglett.8b00228

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of cyclic imidazolidines via two N-C bond-forming sequences has been developed. The transformation goes through a (3 + 2)-cycloaddition reaction in the presence of catalytic amounts of palladium by combining several vinyl aziridines and cyclic N-sulfonyl imines. Interestingly, the use of LiCl as additive allowed the improvement of diastereoselectivities when less encumbered substrates were used. The imidazolidine derivatives that bear aminal cores are isolated in high yields (15 examples, up to 96% yield) and diastereoselectivities (up to >20:1).

引用

页码：1444 / 1447

页数：4

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