Communications

Biomass-based enantioselective approach to 1,2-di(furan-2-yl)ethane-1,2-diamine and its derivatives

K. V. Vasechkin^ab, R. A. Kovalevsky^a, A. S. Kucherenko^a, A. R. Romanenko^c, A. A. Korlyukov^c, S. G. Zlotin<sup>a

a</sup> N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
^b A. P. Nelubin Institute of Pharmacy, I. M. Sechenov First Moscow State Medical University, 119991 Moscow, Russian Federation
^c A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119334 Moscow, Russian Federation

Аннотация: A practical method for the synthesis of (S,S)- and (R,R)-1,2-di(furan-2-yl)ethane-1,2-diamine antipodes in a multigram scale is based on the stereoselective reaction of furfural, a biomass processing product, with commercially available enantiomers of 1,2-bis(2-hydroxyphenyl)ethane-1,2-diamine under green chemistry conditions. Simple chemical transformations of the (S,S)-enantiomer were not accompanied by racemization and did not require chromatographic purification of the products. In this way, chiral derivatives of 2,3-diaminosuccinic acid exhibiting antimicrobial properties, and ketopiperazine, a structural fragment of some biologically active compounds, were obtained.

Ключевые слова: biomass conversion, enantioselective synthesis, bioactive compounds, chiral drugs, diaza–Cope rearrangement, 1,2-diamines.

Поступила в редакцию: 14.07.2025
Принята в печать: 11.08.2025

Язык публикации: английский

DOI: 10.71267/mencom.7871

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