1.11 Nucleophilic Addition of Nonstabilized Carbanions to Imines and Imine Derivatives

Abstract

This chapter summarizes various state-of-the-art methods to generate α-chiral amines by the nucleophilic addition of nonstabilized carbanions to imine derivatives. The first part of the chapter focuses on methods in which chiral imines react with nucleophiles to generate diastereomeric amines. The relative diastereocontrol is usually excellent when suitable conditions are selected. This section also includes a discussion of chiral auxiliary-based methods. The last section of the chapter describes the most effective asymmetric catalytic methods to achieve this transformation. Each section highlights the best methods available depending on the nature of carbanion used (sp3 vs. sp2 vs. sp carbanion).