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Catalytic stereoconvergent synthesis of homochiral ▫$\beta-CF_3$▫, ▫$\beta-SCF_3$▫, and ▫$\beta-OCF_3$▫ benzylic alcoholsCotman, Andrej Emanuel ...We describe an efficient catalytic strategy for enantio- and diastereoselective synthesis of homochiral β-CF3, β-SCF3, and β-OCF3 benzylic alcohols. The approach is based on dynamic kinetic ... resolution (DKR) with Noyori–Ikariya asymmetric transfer hydrogenation leading to simultaneous construction of two contiguous stereogenic centers with up to 99.9% ee, up to 99.9:0.1 dr, and up to 99% isolated yield. The origin of the stereoselectivity and racemization mechanism of DKR is rationalized by density functional theory calculations. Applicability of the previously inaccessible chiral fluorinated alcohols obtained by this method in two directions is further demonstrated: As building blocks for pharmaceuticals, illustrated by the synthesis of heat shock protein 90 inhibitor with in vitro anticancer activity, and in particular, needle-shaped crystals of representative stereopure products that exhibit either elastic or plastic flexibility, which opens the door to functional materials based on mechanically responsive chiral molecular crystals.Source: ACS Organic & Inorganic Au. - ISSN 2694-247X (Vol. 2, iss. 5, 2022, str. 396-404)Type of material - e-article ; adult, seriousPublish date - 2022Language - englishCOBISS.SI-ID - 111499267
Author
Cotman, Andrej Emanuel |
Dub, pavel |
Sterle, Maša |
Lozinšek, Matic, kemik |
Dernovšek, Jaka |
Zajec, Živa, farmacevtka |
Zega, Anamarija |
Tomašič, Tihomir |
Cahard, Dominique
Topics
adaptive crystals |
asymmetric catalysis |
density functional calculations |
drug design |
fluorine hydrogenation |
kinetic resolution |
ruthenium
Author | Cotman, Andrej Emanuel ... |
Title | Catalytic stereoconvergent synthesis of homochiral ▫$\beta-CF_3$▫, ▫$\beta-SCF_3$▫, and ▫$\beta-OCF_3$▫ benzylic alcohols |
Publication date | |
COBISS.SI-ID | 111499267 |
Publication version in repository | Publisher's version |
Publication licence | Unidentified |
Embargo | Immediate publication for public |
Project(s) from which the publication was funded
Title | Acronym | Project ID | Funder |
---|---|---|---|
Farmacevtska kemija: načrtovanje, sinteza in vrednotenje učinkovin | P1-0208-2015 |
Javna agencija za znanstvenoraziskovalno in inovacijsko dejavnost Republike Slovenije |
|
Modularna asimetrična totalna sinteza biološko aktivnih naravnih produktov z več kiralnimi centri | Z1-2635-2020 |
Javna agencija za znanstvenoraziskovalno in inovacijsko dejavnost Republike Slovenije |
|
Razvoj novih zaviralcev Hsp90 s protitumornim delovanjem | J1-1717-2019 |
Javna agencija za znanstvenoraziskovalno in inovacijsko dejavnost Republike Slovenije |
|
Challenging the Oxidation-State Limitations of the Periodic Table via High-Pressure Fluorine Chemistry | HiPeR-F | 950625 |
European Commission |
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Link |
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https://pubs.acs.org/doi/10.1021/acsorginorgau.2c00019 |
https://repozitorij.uni-lj.si/IzpisGradiva.php?id=141984 |
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Database name | Field | Year |
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Links to authors' personal bibliographies | Links to information on researchers in the SICRIS system |
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Cotman, Andrej Emanuel | 37459 |
Dub, pavel | |
Sterle, Maša | 53583 |
Lozinšek, Matic, kemik | 30880 |
Dernovšek, Jaka | 54784 |
Zajec, Živa, farmacevtka | 53670 |
Zega, Anamarija | 18633 |
Tomašič, Tihomir | 28334 |
Cahard, Dominique |
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