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

Jae Sang Ryu, Tobin J Marks, Frank E. McDonald

Research output: Contribution to journalArticle

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Abstract

(equation presented) 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 (η5-Me5C5)2LnCH(TMS)2 (Ln = La, Sm), [Me2Si(η5-Me4C5) 2]NdCH(TMS)2, [Et2Si(η5Me4C5)(η 5-C5H4)]NdCH(TMS)2, and [Me2Si(η5-Me4C5)( tBuN)]-LnE(TMS)2 (Ln = Sm, Y, Yb, Lu; E = N, CH) as precatalysts. [Me2Si(η5-Me4C5)( tBuN)]LnE(TMS)2 mediates intramolecular hydroanimation/ cyclization of sterically demanding amino-olefins to afford disubstituted pyrrolidines in high diastereoselectivity (translcis = 16/1) and in good to excellent yield.

Original languageEnglish
Pages (from-to)3091-3094
Number of pages4
JournalOrganic Letters
Volume3
Issue number20
DOIs
Publication statusPublished - Oct 4 2001

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Pyrrolidines
Cyclization
Alkenes
alkenes
Amines
amines
Piperidines
piperidine
methylidyne

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Organolanthanide-catalyzed intramolecular hydroamination/ cyclization of amines tethered to 1,2-disubstituted alkenes. / Ryu, Jae Sang; Marks, Tobin J; McDonald, Frank E.

In: Organic Letters, Vol. 3, No. 20, 04.10.2001, p. 3091-3094.

Research output: Contribution to journalArticle

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abstract = "(equation presented) 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 (η5-Me5C5)2LnCH(TMS)2 (Ln = La, Sm), [Me2Si(η5-Me4C5) 2]NdCH(TMS)2, [Et2Si(η5Me4C5)(η 5-C5H4)]NdCH(TMS)2, and [Me2Si(η5-Me4C5)( tBuN)]-LnE(TMS)2 (Ln = Sm, Y, Yb, Lu; E = N, CH) as precatalysts. [Me2Si(η5-Me4C5)( tBuN)]LnE(TMS)2 mediates intramolecular hydroanimation/ cyclization of sterically demanding amino-olefins to afford disubstituted pyrrolidines in high diastereoselectivity (translcis = 16/1) and in good to excellent yield.",
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AB - (equation presented) 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 (η5-Me5C5)2LnCH(TMS)2 (Ln = La, Sm), [Me2Si(η5-Me4C5) 2]NdCH(TMS)2, [Et2Si(η5Me4C5)(η 5-C5H4)]NdCH(TMS)2, and [Me2Si(η5-Me4C5)( tBuN)]-LnE(TMS)2 (Ln = Sm, Y, Yb, Lu; E = N, CH) as precatalysts. [Me2Si(η5-Me4C5)( tBuN)]LnE(TMS)2 mediates intramolecular hydroanimation/ cyclization of sterically demanding amino-olefins to afford disubstituted pyrrolidines in high diastereoselectivity (translcis = 16/1) and in good to excellent yield.

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