Detailed Information on Publication Record
2023
Enantioselective trihalohydroxyalkylation of activated phenols
OTEVŘEL, Jan, David ŠVESTKA and Pavel BOBÁĽBasic information
Original name
Enantioselective trihalohydroxyalkylation of activated phenols
Name in Czech
Enantioselektivní trihalohydroxyalkylace aktivovaných fenolů
Authors
OTEVŘEL, Jan (203 Czech Republic, belonging to the institution), David ŠVESTKA (203 Czech Republic, belonging to the institution) and Pavel BOBÁĽ (703 Slovakia, belonging to the institution)
Edition
57th Advances in Organic, Bioorganic and Pharmaceutical Chemistry Liblice 2023. 2023
Other information
Language
English
Type of outcome
Prezentace na konferencích
Field of Study
30104 Pharmacology and pharmacy
Country of publisher
Czech Republic
Confidentiality degree
není předmětem státního či obchodního tajemství
References:
RIV identification code
RIV/00216224:14160/23:00132225
Organization unit
Faculty of Pharmacy
Keywords (in Czech)
Enantioselectivní organokatalýza; Reakce aldolového typu
Keywords in English
Enantioselective Organocatalysis; Aldol-Type Reactions
Změněno: 4/4/2024 19:17, Mgr. Daniela Černá
Abstract
V originále
At the onset of our work, the asymmetric trihalohydroxyalkylation of activated phenols has only been described on a few substrates using a stoichiometric amount of the chiral Lewis acid. To identify a competent organocatalyst for this Friedel–Crafts reaction, an extensive screening comprising 41 organocatalysts was performed, and the 3,5-dinitrobenzoyl derivative of 9-amino-epi-cinchonidine was identified as a lead catalyst candidate. By employing just 10–20 mol% of the chiral organocatalyst, our process offered a reasonably general scope regarding both the nucleophilic and electrophilic reaction partners. About 30 enantioenriched products were isolated in fair yields and good to excellent enantioselectivities. Moreover, several stereoselective downstream transformations of the chiral adducts were discovered, which opened up a chemical space for their possible applications in organic synthesis. Retro-aldol cleavage and dehydration, together with the gaseous or low-boiling nature of trihaloacetaldehydes, represented just a fraction of the challenges we faced to achieve high enantioselectivity.
Links
| EF19_073/0016943, research and development project |
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| LM2023042, research and development project |
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| MUNI/IGA/0916/2021, interní kód MU |
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