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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/68378271:_____/22:00551348 RIV/00216208:11310/22:10447265 RIV/00216208:11320/22:10447265

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2022

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Advanced Synthesis & Catalysis

ISSN

1615-4150

e-ISSN

1615-4169

Svazek periodika

364

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

930-937

Kód UT WoS článku

000734112900001

EID výsledku v databázi Scopus

2-s2.0-85121549303