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Titanocene(III)-catalyzed conversion of N-(epoxyalkyl)anilines into indolines

By John P. Maciejewski and Peter Wipf


Dedicated to Prof. Heinz Heimgartner on the occasion of his 70th birthday Densely substituted indolines and azaindolines can be obtained by the titanocene(III) chloride catalyzed reductive opening of N-(oxiran-2-ylmethyl)anilines. The reaction optimization, substrate scope, and limitations are discussed, and a mechanistic pathway for the epoxideopening rearrangement is proposed. Keywords: Indoline, titanocene dichloride, N-(epoxyalkyl) aniline, radical additio

Year: 2011
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