Synthesis and Use ofN-(Trimethylsilyl)imines

Abstract

The introduction of aminic nitrogen in organic molecules has been achieved in many different ways, one of the most popular being the use of imines. The main disadvantage of these starting materials lies in the difficulty of synthesising and using imines of ammonia, due to their instability, which results in their tendency to trimerize, giving the corresponding triazine. Recently a new class of imines, the N-metalloimines, a stable form of the corresponding elusive imines of ammonia, has found very useful applications in the synthesis of nitrogen-containing organic compounds. This review will cover the syntheses and applications of N-(trialkylsilyl)imines. It is not intended to be a comprehensive review of the literature; rather it is intended to highlight novel and potentially useful applications. In this context, particular emphasis will be devoted to methodologies which could be easily scaled up to kilogram scale. The synthesis of important small-ring heterocycles such as aziridines, β-lactams, pyrrolines, and piperidines and hetero-Diels−Alder derived compounds will be reviewed. Some aspects of the synthesis of commercially interesting acyclic compounds, such as amines, aminols, nitriles, and amino acids, obtained using N-(trialkylsilyl)imines, will be reported.