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@proceedings{2338864,
author = {Otevřel, Jan and Švestka, David and Bobáľ, Pavel},
booktitle = {57th Advances in Organic, Bioorganic and Pharmaceutical Chemistry Liblice 2023.},
keywords = {Enantioselective Organocatalysis; Aldol-Type Reactions},
language = {eng},
title = {Enantioselective trihalohydroxyalkylation of activated phenols},
url = {https://mab.uochb.cas.cz/liblice2023/programme.php},
year = {2023}
}
TY - CONF
ID - 2338864
AU - Otevřel, Jan - Švestka, David - Bobáľ, Pavel
PY - 2023
TI - Enantioselective trihalohydroxyalkylation of activated phenols
KW - Enantioselective Organocatalysis
KW - Aldol-Type Reactions
UR - https://mab.uochb.cas.cz/liblice2023/programme.php
N2 - 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.
ER -
OTEVŘEL, Jan, David ŠVESTKA and Pavel BOBÁĽ. Enantioselective trihalohydroxyalkylation of activated phenols. In \textit{57th Advances in Organic, Bioorganic and Pharmaceutical Chemistry Liblice 2023.}. 2023.
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