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

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

doi:10.1021/ol010129t

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

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

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

132 Scopus citations

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 language	English
Pages (from-to)	3091-3094
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	20
DOIs	https://doi.org/10.1021/ol010129t
State	Published - 4 Oct 2001

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

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.",

author = "Ryu, {Jae Sang} and Marks, {Tobin J.} and McDonald, {Frank E.}",

year = "2001",

month = oct,

day = "4",

doi = "10.1021/ol010129t",

language = "English",

volume = "3",

pages = "3091--3094",

journal = "Organic Letters",

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T1 - Organolanthanide-catalyzed intramolecular hydroamination/ cyclization of amines tethered to 1,2-disubstituted alkenes

AU - Ryu, Jae Sang

AU - Marks, Tobin J.

AU - McDonald, Frank E.

PY - 2001/10/4

Y1 - 2001/10/4

N2 - (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.

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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U2 - 10.1021/ol010129t

DO - 10.1021/ol010129t

M3 - Article

C2 - 11574002

AN - SCOPUS:0035807535

SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

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

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