Stereoselective cyclopropanation of boron dipyrromethene (BODIPY) derivatives by an organocascade reaction

0551348 - FZÚ 2023 RIV DE eng J - Článek v odborném periodiku
Dočekal, V. - Koberová, T. - Hrabovský, Jan - Vopálenská, A. - Gyepes, Robert - Císařová, I. - Rios, R. - Veselý, J.
Stereoselective cyclopropanation of boron dipyrromethene (BODIPY) derivatives by an organocascade reaction.
Advanced Synthesis & Catalysis. Roč. 364, č. 5 (2022), s. 930-937. ISSN 1615-4150. E-ISSN 1615-4169
Grant CEP: GA MŠMT EF15_003/0000445
Grant ostatní: OP VVV - BIATRI(XE) CZ.02.1.01/0.0/0.0/15_003/0000445
Institucionální podpora: RVO:68378271 ; RVO:61388955
Klíčová slova: asymmetric catalysis * organocatalysis * dyes/pigments * cyclization * domino reactions
Obor OECD: Optics (including laser optics and quantum optics); Physical chemistry (UFCH-W)
Impakt faktor: 5.4, rok: 2022
Způsob publikování: Omezený přístup
https://doi.org/10.1002/adsc.202101286

The synthesis of enantiopure chiral boron dipyrromethenes (BODIPYs) is of importance due the intrinsic properties of BODIPYs as fluorophores that could be used as probes for molecular sensing. The present study reports an asymmetric organocatalytic cascade reaction of meso-chloromethyl BODIPY derivatives with α,β-unsaturated aldehydes catalyzed by a chiral secondary amine. The corresponding BODIPY-derived cyclopropanes were produced in isolated yields 66–98%, and with diastereomeric ratios 3/2->20/1, and 92–99% ee for major diastereomer. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding optically pure compounds. In addition, a study explaining the reaction mechanism (DFT computations) and photophysical characterization of all enantioenriched products were accomplished.
Trvalý link: http://hdl.handle.net/11104/0329161