Organolanthanide-catalyzed intramolecular hydroamination/cyclization of amines tethered to 1,2-disubstituted alkenes

被引：118

作者：

Ryu, JS

Marks, TJ

McDonald, FE

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

[2] Emory Univ, Atlanta, GA 30322 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 20期

关键词：

D O I：

10.1021/ol010129t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] This contribution reports the organolanthanide-catalyzed intramolecular hydroamination/cyclization of amines tethered to 1,2-disubstituted alkenes to afford the corresponding mono- and disubstituted pyrrolidines and piperidines by using coordinatively unsaturated complexes of the type (eta (5)-Me5C5)(2)LnCH(TMS)(2) (Ln = La, Sm), [Me2Si(eta (5)-Me4C5)(2)]NdCH(TMS)(2), [Et2Si(eta (5)-Me4C5)(eta (5)-C5H4)]NdCH(TMS)(2), and [Me2Si(eta (5)-Me4C5)((BuN)-Bu-t)]-LnE(TMS)(2) (Ln = Sm, Y, Yb, Lu; E = N, CH) as precatalysts. [Me2Si(eta (5)-Me4C5)((BuN)-Bu-t)]LnE(TMS)(2) mediates intramolecular hydroamination/cyclization of sterically demanding amino-olefins to afford disubstituted pyrrolidines in high diastereoselectivity (trans/cis = 16/1) and in good to excellent yield.

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页码：3091 / 3094

页数：4

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