Synthesis of 1-(adamantan-1-yl)propan-1,2-diamine and chiral ligands based thereon

Abstract

Racemic 1-(adamantan-1-yl)propan-1,2-diamine which was resolved with l-malic acid was obtained from trans-2-(adamantan-1-yl)-3-methylaziridine. The isolated (1 S ,2 R )-isomer was derivatized with benzyl. Enantiomeric excess of (2 S ,3 R )-2-(adamantan-1-yl)-3-methyl-5,6-diphenyl-2,3-dihydropyrazine was determined by HPLC. (4 S ,5 R )-4-(Adamantan-1-yl)-5-methylimidazolidine-2-thione was synthesized by the reaction of (1 S ,2 R )-diamine with carbon disulfide; absolute configuration was determined by X-ray diffraction analysis. Ligands were synthesized on the basis of racemic and chiral (1 S ,2 R )-1-(adamantan-1-yl)propan-1,2-diamines. The catalytic activity complexes were studied using Michael, Henri and epoxidation model reactions. For the model reaction of Henri stereodivergence was noted when using ligands of a similar structure.