Electrophilic Aminations with Oxaziridines

Cyclohexanespiro-3′-oxaziridine transfers its NH group to N-, O-, S- and C-nuceophiles, thus making possible the syntheses of azines, hydrazines, diaziridines, hydrazino acids, N-aminopeptides, aziridines, triazanes, O-alkylhydroxylamines, sulfenamides, thiooximes, and aminodicarboxylic acid derivatives. There is also report on some subsequent reactions of the products of amination as well as on acyl-N transfer by 2-acyloxaziridines. This review is based mainly on the results of the authors. 1. Introduction 2. General Aspects 2.1. Synthesis of Oxaziridines 2.2. Some General Aspects of Amination 3. Amination of N-Nucleophiles 3.1. Amination of Secondary Amines 3.2. Amination of Primary Amines, Amino Acid and Peptide Derivatives 3.3. Amination of Tertiary Amines 3.4. Amination of Ammonia 4. Acylamidations by 2-Acyloxaziridines 4.1. Intermolecular Acylamidations 4.2. Intramolecular Acylamidations 5. Amination of O-Nucleophiles 6. Amination of S-Nucleophiles 6.1. Preparation of Sulfenamides and Thiooximes 6.2. Ring Closures Following S-Amination 6.3. Cyclohexanone Thiooxime Rearrangement 6.4. Subsequent Reactions with Loss of Sulfur 7. Amination of C-Nucleophiles 7.1. Amination of C - H Acidic Compounds 7.2. Epamination of Olefins 8. Comparison of Oxaziridines with Other Aminating Reagents