Organolanthanide-catalyzed intramolecular hydroamination/cyclization/bicyclization of sterically encumbered substrates. Scope, selectivity, and catalyst thermal …

JS Ryu, TJ Marks, FE McDonald

Index: Ryu, Jae-Sang; Marks, Tobin J.; McDonald, Frank E. Journal of Organic Chemistry, 2004 , vol. 69, # 4 p. 1038 - 1052

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Citation Number: 144

Abstract

This paper reports the organolanthanide-catalyzed intramolecular hydroamination/ cyclization of amine-tethered unactivated 1, 2-disubstituted alkenes to afford the corresponding mono-and disubstituted pyrrolidines and piperidines using coordinatively unsaturated complexes of the type (η 5-Me5C5) 2LnCH (TMS) 2 (Ln= La, Sm),[Me2Si (η 5- Me4C5) 2] SmCH (TMS) 2, and [Me2Si (η5-Me4C5)(tBuN)] LnE (TMS) 2 (Ln= Sm, Y, Yb, ...