Stereoselective cyclopropanation of boron dipyrromethene (BODIPY) derivatives by an organocascade reaction
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F22%3A00551348" target="_blank" >RIV/61388955:_____/22:00551348 - isvavai.cz</a>
Alternative codes found
RIV/68378271:_____/22:00551348 RIV/00216208:11310/22:10447265 RIV/00216208:11320/22:10447265
Result on the web
<a href="https://doi.org/10.1002/adsc.202101286" target="_blank" >https://doi.org/10.1002/adsc.202101286</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/adsc.202101286" target="_blank" >10.1002/adsc.202101286</a>
Alternative languages
Result language
angličtina
Original language name
Stereoselective cyclopropanation of boron dipyrromethene (BODIPY) derivatives by an organocascade reaction
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10403 - Physical chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Advanced Synthesis & Catalysis
ISSN
1615-4150
e-ISSN
1615-4169
Volume of the periodical
364
Issue of the periodical within the volume
5
Country of publishing house
DE - GERMANY
Number of pages
9
Pages from-to
930-937
UT code for WoS article
000734112900001
EID of the result in the Scopus database
2-s2.0-85121549303