Stereoselective Cyclopropanation of Boron Dipyrromethene (BODIPY) derivatives by an organocascade reaction
Stereoselective Cyclopropanation of Boron Dipyrromethene (BODIPY) derivatives by an organocascade reaction
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.
Vojtech, Docekal
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Koberová, Tereza
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Hrabovský, Jan
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Vopálenská, Andrea
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Gyepes, Róbert
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Císařová, Ivana
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Rios, Ramon
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Veselý, Jan
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Vojtech, Docekal
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Koberová, Tereza
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Hrabovský, Jan
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Vopálenská, Andrea
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Gyepes, Róbert
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Císařová, Ivana
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Rios, Ramon
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Veselý, Jan
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Vojtech, Docekal, Koberová, Tereza, Hrabovský, Jan, Vopálenská, Andrea, Gyepes, Róbert, Císařová, Ivana, Rios, Ramon and Veselý, Jan
(2021)
Stereoselective Cyclopropanation of Boron Dipyrromethene (BODIPY) derivatives by an organocascade reaction.
Advanced Synthesis & Catalysis.
(doi:10.1002/adsc.202101286).
Abstract
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.
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2021_Docekal_B_MainText_20211018f
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Accepted/In Press date: 30 November 2021
e-pub ahead of print date: 20 December 2021
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Local EPrints ID: 454841
URI: http://eprints.soton.ac.uk/id/eprint/454841
ISSN: 1615-4150
PURE UUID: d29da837-58b7-4793-8186-3dcd99db58f9
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Date deposited: 24 Feb 2022 21:57
Last modified: 17 Mar 2024 07:05
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Contributors
Author:
Docekal Vojtech
Author:
Tereza Koberová
Author:
Jan Hrabovský
Author:
Andrea Vopálenská
Author:
Róbert Gyepes
Author:
Ivana Císařová
Author:
Jan Veselý
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