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A Divergent Mechanistic Course of Pd(0)-Catalyzed Aza-Claisen Rearrangement and Aza-Rautenstrauch-Type Cyclization of N-Allyl Ynamides

A fascinating mechanistic study of ynamido−palladium−π-allyl complexes is described that features isolation of a unique silyl ketenimine via aza-Claisen rearrangement, which can be accompanied by an unusual thermal N-to-C 1,3-Ts shift in the formation of tertiary nitriles and a novel cyclopentenimine formation via a palladium-catalyzed aza-Rautenstrauch-type cyclization pathway.

Authors:   Kyle A. DeKorver; Richard P. Hsung; Andrew G. Lohse; Yu Zhang
Journal:   Organic Letters
Year:   2010
DOI:   10.1021/ol100446p
Publication date:   09-Apr-2010
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