Synthesis of Chiral Ligands on the Basis of 1-(Adamantan-1-yl)ethane-1,2-diamine

The reduction of 1-(adamantan-1-yl)-2-azidoethan-1-one oxime with LiAlH 4 gave racemic 1-(adamantan-1-yl)ethane-1,2-diamine, which was resolved with l-tartaric acid. The individual enantiomer was obtained with a yield of 20% and derivatized into 4-(adamantan-1-yl)imidazolidine-2-thione. The absolute...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2021-02, Vol.57 (2), p.226-236
Main Authors: Man’kova, P. A., Reznikov, A. N., Shiryaev, V. A., Baimuratov, M. R., Rybakov, V. B., Klimochkin, Yu. N.
Format: Article
Language:English
Subjects:
Catalytic activity
Chemistry
Chemistry and Materials Science
Copper compounds
Diamines
Enantiomers
Epoxidation
Ethane
Ligands
Lithium aluminum hydrides
Manganese
Organic Chemistry
Tartaric acid
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Summary:The reduction of 1-(adamantan-1-yl)-2-azidoethan-1-one oxime with LiAlH 4 gave racemic 1-(adamantan-1-yl)ethane-1,2-diamine, which was resolved with l-tartaric acid. The individual enantiomer was obtained with a yield of 20% and derivatized into 4-(adamantan-1-yl)imidazolidine-2-thione. The absolute configuration of the derivatized diamine was established by X-ray diffraction analysis, and the enantiomeric excess (96%) was determined using HPLC. Diamine and diimine ligands were synthesized on the basis of racemic and chiral (1 S )-1-(adamantan-1-yl)ethane-1,2-diamine. The catalytic activity nickel(II), copper(II), and manganese(II) complexes were studied in model Michael, Henry, and epoxidation reactions.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428021020135