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Naji, M. |
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Motta, Antonella |
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Aletan, Dirar |
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Mohamed, Tarek |
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Ertürk, Emre |
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Taccardi, Nicola |
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Kononenko, Denys |
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Petrov, R. H. | Madrid |
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Alshaaer, Mazen | Brussels |
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Bih, L. |
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Casati, R. |
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Muller, Hermance |
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Kočí, Jan | Prague |
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Šuljagić, Marija |
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Kalteremidou, Kalliopi-Artemi | Brussels |
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Azam, Siraj |
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Ospanova, Alyiya |
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Blanpain, Bart |
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Ali, M. A. |
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Popa, V. |
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Rančić, M. |
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Ollier, Nadège |
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Azevedo, Nuno Monteiro |
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Landes, Michael |
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Rignanese, Gian-Marco |
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Justyniak, Iwona
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Topics
Publications (9/9 displayed)
- 2024Unprecedented Richness of Temperature‐ and Pressure‐Induced Polymorphism in 1D Lead Iodide Perovskitecitations
- 2023A modular design approach to polymer-coated ZnO nanocrystals
- 2021From Uncommon Ethylzinc Complexes Supported by Ureate Ligands to Water-Soluble ZnO Nanocrystals: A Mechanochemical Approachcitations
- 2021Towards deeper understanding of multifaceted chemistry of magnesium alkylperoxidescitations
- 2021ZnO Nanoplatelets with Controlled Thickness: Atomic Insight into Facet‐Specific Bimodal Ligand Binding Using DNP NMRcitations
- 2017Lipase-catalyzed kinetic resolution approach toward enantiomerically enriched 1-(β-hydroxypropyl)indolescitations
- 2016Alkylzinc diorganophosphates: synthesis, structural diversity and unique ability to incorporate zincoxane unitscitations
- 2014A solvothermal and mechanochemical strategy for the construction of chiral N,N-ditopic metalloligands: Oxygenation process of a Cu(I)X/Quinine systemcitations
- 2013Benzoxaborolate ligands in group 13 metal complexescitations
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article
Lipase-catalyzed kinetic resolution approach toward enantiomerically enriched 1-(β-hydroxypropyl)indoles
Abstract
In a route towards enantiomerically enriched 1-(β-hydroxypropyl)indoles, which are potentially useful building blocks for high value-added chemicals synthesis, a kinetic resolution approach by means of lipase-catalyzed enantioselective acylation as well as hydrolysis/methanolysis has been elaborated for the first time. The enzymatic resolution of chiral N-substituted indole-based sec-alcohols was successfully accomplished, yielding both enantiomeric forms of the employed derivatives with up to >99% enantiomeric purity via an enantioselective transesterification under mild reaction conditions. The most selective resolutions were obtained using fungal (CAL-B and TLL) and bacterial (PFL and BCL) lipases and vinyl acetate as the acyl group donor. The synthetic protocol described herein is very simple, user-friendly and efficient, thus paving the way for future access towards more complex compounds of this type. The absolute configurations of novel enantiomeric derivatives, and thus stereoselectivity of the described enzymatic reactions were confirmed by application of CDA-based NMR methodology and single-crystal X-ray diffraction analysis.