H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters

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Authors
Niedbała, Patryk
Majdecki, Maciej
Grodek, Piotr
Jurczak, Janusz
Date
2022
Journal Title
Journal ISSN
Volume Title
Publisher
MDPI
License
Creative Commons License
Creative Commons Attribution 4.0 International License
Abstract
In this work, we would like to present the development of a highly optimized method for generating the quaternary stereogenic centers in β-keto esters. This enantioselective phase-transfer alkylation catalyzed by hybrid Cinchona catalysts allows for the efficient generation of the optically active products with excellent enantioselectivity, using only 1 mol% of the catalyst. The vast majority of phase-transfer catalysts in asymmetric synthesis work by creating ionic pairs with the nucleophile-attacking anionic substrate. Therefore, it is a sensible approach to search for new methodologies capable of introducing functional groups into the precursor’s structure, maintaining high yields and enantiomeric purity.
Description
Keywords
phase-transfer catalysis    organocatalysis    enantioselectivity    Cinchona catalysts    alkylation
Citation
Niedbała, P.; Majdecki, M.;Grodek, P.; Jurczak, J. H-Bond Mediated Phase-Transfer Catalysis: Eantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters. Molecules 2022, 27, 2508. https://doi.org/10.3390/molecules27082508
URI
https://open.icm.edu.pl/handle/123456789/21379
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