Organolanthanide-Catalyzed Intramolecular Hydroamination/Cyclization of Amines Tethered to 1,2-Disubstituted Alkenes

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 (η 5-Me5C5)2Ln...

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Bibliographic Details
Published in:Organic letters 2001-10, Vol.3 (20), p.3091-3094
Main Authors: Ryu, Jae-Sang, Marks, Tobin J, McDonald, Frank E
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Amines - chemistry
Lanthanoid Series Elements - chemistry
Molecular Conformation
Organometallic Compounds - chemistry
Piperidines - chemical synthesis
Pyrrolidines - chemical synthesis
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Summary: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 (η 5-Me5C5)2LnCH(TMS)2 (Ln = La, Sm), [Me2Si(η 5-Me4C5)2]NdCH(TMS)2, [Et2Si(η 5-Me4C5)(η 5-C5H4)]NdCH(TMS)2, and [Me2Si(η 5-Me4C5)( t BuN)]LnE(TMS)2 (Ln = Sm, Y, Yb, Lu; E = N, CH) as precatalysts. [Me2Si(η 5-Me4C5)( t BuN)]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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol010129t