Enantioselective synthesis of aziridines using asymmetric transfer hydrogenation as a precursor for chiral derivatives used as bonding agent for rocket solid propellants

• Published in: Química nova Vol. 25; no. 6a; pp. 921 - 925
• Main Authors: Kawamoto, Aparecida M., Wills, Martin
• Format: Journal Article
• Language: English
• Published: Sociedade Brasileira de Química 01-11-2002
• Subjects: aziridines; bonding agent; transfer hydrogenation
• ISSN: 0100-4042; 0100-4042; 1678-7064
• DOI: 10.1590/S0100-40422002000600007

A rapid, expedient and enantioselective method for the synthesis of beta-hydroxy amines and monosubstituted aziridines in up to 99% e.e., via asymmetric transfer hydrogenation of a-amino ketones and cyclisation through treatment with tosyl chloride and base, is described. (1R,2R)-N-(para-toluenesulfonyl)-1,2-ethylenediamine with formic acid has been utilised as a ligand for the Ruthenium (II) catalysed enantioselective transfer hydrogenation of the ketones.The chiral 2-methyl aziridine, which is a potentially more efficient bonding agent for Rocket Solid Propellant has been successfully achieved.