Inserting a radical label at position 9 of bispidine using the Horner—Wadsworth—Emmons reaction to create a spin-labeled organocatalyst

Inserting a radical label at position 9 of bispidine using the Horner—Wadsworth—Emmons reaction to create a spin-labeled organocatalyst Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2025, Volume: 74, Number: 7, Pages: 2026-2037 Pages count : 12 DOI: 10.1007/s11172-025-4687-2

Authors

Ermakov M.O. ^1,2 , Medvedko A.V. ² , Zakirov A.M. ² , Tretyakov E.V. ² , Vatsadze S.Z. ²

Affiliations

1	Department of Chemistry, Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

A bispidine derivative containing a paramagnetic moiety at position 9 was first synthesized by the Horner—Wadsworth—Emmons reaction between bispidine and a suitable radical-labeled reagent. The structures of diethyl {2-[(2,2,6,6-tetramethyl-1-oxylpiperidin-4-yl)amino]-2-oxoethyl}phosphonate, the free radical used as a reagent in this reaction, and 2-(3-benzyl-3,7-diazabicyclo[3.3.1]nonan-9-ylidene)-N-(2,2,6,6-tetramethyl-1-oxylpiperidin-4-yl)acetamide, the target radical, were confirmed using a combination of physicochemical analysis methods (mass spectrometry, EPR spectroscopy, and X-ray diffraction). Using the obtained spin-labeled catalyst, the EPR monitoring of the Michael reaction (addition of diethyl malonate to nitrostyrene) was carried out for the first time, which made it possible to formulate principles for designing catalysts with reporter groups.

Ermakov M.O. , Medvedko A.V. , Zakirov A.M. , Tretyakov E.V. , Vatsadze S.Z.
Inserting a radical label at position 9 of bispidine using the Horner—Wadsworth—Emmons reaction to create a spin-labeled organocatalyst
Russian Chemical Bulletin. 2025. V.74. N7. P.2026-2037. DOI: 10.1007/s11172-025-4687-2 WOS Scopus OpenAlex

Web of science:	WOS:001554001100016
Scopus:	2-s2.0-105013295627
OpenAlex:	W4413461989

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