We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Synthesis of 1-(Adamantan-1-yl)propane-1,2-diamine and Chiral Ligands Based Thereon.
- Authors
Mankova, P. A.; Reznikov, A. N.; Shiryaev, V. A.; Tkachenko, I. M.; Klimochkin, Yu. N.
- Abstract
Racemic 1-(adamantan-1-yl)propane-1,2-diamine was synthesized from trans-2-(adamantan-1-yl)-3-methylaziridine, and its optical resolution was achieved with the use of L-malic acid. The isolated (1S,2R)-stereoisomer was derivatized with benzil, and enantiomeric purity of the resulting (2S,3R)-2-(adaman-tan-1-yl)-3-methyl-5,6-diphenyl-2,3-dihydropyrazine was determined by chiral HPLC. The reaction of (1S,2R)-1-(adamantan-1-yl)propane-1,2-diamine with carbon disulfide gave (4S,5R)-4-(adamantan-1-yl)-5-methylimidazolidine-2-thione whose absolute configuration was established by X-ray analysis. Racemic and optically pure (1S,2R)-1-(adamantan-1-yl)propane-1,2-diamines were used to obtain ligands and their metal complexes, and the latter were studied as catalysts in model epoxidation, Michael, and Henry reactions. Enantiodivergence was observed in the Henry reaction catalyzed by structurally related ligands.
- Subjects
DIAMINES; NITROALDOL reactions; ENANTIOMERIC purity; LIGANDS (Chemistry); OPTICAL resolution; CARBON disulfide
- Publication
Russian Journal of Organic Chemistry, 2023, Vol 59, Issue 3, p383
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428023030053