Abstract
N -Phosphinoylimines have recently begun to attract significant attention from synthetic chemists for the preparation of nitrogen-containing molecules. Several methods have been developed for the synthesis, or in situ generation, of these reactive electrophilic species. N -Phosphinoylimines undergo a wide range of reactions, including nucleophilic additions and cycloadditions. These imines are also effective electrophiles in a number of diastereoselective and enantioselective reactions. An advantage of using N -phosphinoylimines is that the reaction products can be easily deprotected under mild acidic conditions, leading to amines. This review outlines the preparation and uses of N -phosphinoylimines with particular emphasis on their applications in stereoselective processes.
1 Introduction
2 Preparation of N -Phosphinoylimines
3 Addition of Nucleophiles to N -Phosphinoylimines
3.1 Heteroatom Nucleophiles
3.2 Hydride
3.3 Carbon Nucleophiles
3.3.1 Addition of Organometallics
3.3.2 Chiral Auxiliary-Controlled Addition of Organometallics
3.3.3 Enantioselective Addition Using Chiral Ligands
3.3.4 Mannich and Related Reactions
3.3.5 Addition of Nitrile Anions
3.3.6 Aza-Henry Reaction
3.3.7 Aza-Baylis-Hillman Reaction
3.3.8 Formation of Aziridines
3.3.9 Miscellaneous Addition Reactions
4 Cycloadditions and Pericyclic Reactions of N -Phosphinoylimines
5 Oxidation of N -Phosphinoylimines to Oxaziridines
6 Conclusion
Key words
imines - amines - diastereoselective synthesis - enantioselective synthesis - chiral catalysts
