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

[GRAPHICS] This contribution reports the organolanthanide-catalyzed intramolecular hyd roamination/cyclization of amines tethered to 1,2-disubstituted alkenes to afford the corresponding mono- and disubstituted pyrrolidines and piperidin es 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), [Et2 Si(eta (5)-Me4C5)(eta (5)-C5H4)]NdCH(TMS)(2), and [Me2Si(eta (5)-Me4C5)((Bu N)-Bu-t)]-LnE(TMS)(2) (Ln = Sm, Y, Yb, Lu; E = N, CH) as precatalysts. [Me2 Si(eta (5)-Me4C5)((BuN)-Bu-t)]LnE(TMS)(2) mediates intramolecular hydroamin ation/cyclization of sterically demanding amino-olefins to afford disubstit uted pyrrolidines in high diastereoselectivity (trans/cis = 16/1) and in go od to excellent yield.