Scope and limitations of the solution and solid phase synthesis of homoallylic amines via N-acyliminium ion reactions

Abstract

The full scope and limitations of solution and solid phase one-pot three component Nacyliminium ion reactions are detailed. After studying the scope in solution with respect to the carbamate, nucleophile and aldehyde component, a 'translation' was made to the solid phase. The solid phase reactions were eventually carried out using the so-called SEC linker system, which was previously developed in our group. In order to maximize the scope of the nucleophile component, additional studies were successfully conducted using two-step processes involving stable N-acyliminium ion precursors.