Aminimide Synthesis Using Concerted Amination Reactions of Alkenes: Scope and Mechanistic Information.

Aminimides are key intermediates in the thermal cycloadditions of suitable alkenyl-hydrazine derivatives. Substrate modifications (β-N,N-dialkyl) allowed the isolation of these reactive intermediates, and the analysis of their stereochemistry provided support for concerted (Cope-type) hydroamination and concerted [3 + 2] aminocarbonylation reaction pathways. This work also establishes the applicability of these approaches to form complex aminimides in moderate to excellent yields.