Detailed Information on Publication Record
2024
Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates
ŠVESTKA, David, Pavel BOBÁĽ, Mario WASER and Jan OTEVŘELBasic information
Original name
Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates
Authors
ŠVESTKA, David (203 Czech Republic, belonging to the institution), Pavel BOBÁĽ (703 Slovakia, belonging to the institution), Mario WASER (40 Austria) and Jan OTEVŘEL (203 Czech Republic, belonging to the institution)
Edition
ACS PUBLICATIONS SYMPOSIUM Catalysis for Organic Synthesis, 2024
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
Organization unit
Faculty of Pharmacy
Keywords in English
Enantioselective organocatalysis; Takemoto catalyst; Formaldehyde
Tags
International impact
Změněno: 25/8/2024 22:41, Mgr. David Švestka
Abstract
V originále
We developed a novel process for the asymmetric transfer hydroxymethylation between formaldehyde surrogates and activated isoindolinones. Bench-stable solid formaldehyde surrogates offer many advantages, such as no water presence, better solubility in organic solvents, and superior reactivity over conventionally used aqueous formalin, paraformaldehyde, or trioxane. However, they have never been systematically tested in asymmetric reactions. After the catalysts screening, the selection of the most suitable surrogate, and reaction conditions optimization, the enantioenriched hydroxymethylated adducts were delivered with good to excellent yields (48–96%) and enantiopurities (81:19 – 97:3 e.r). The substrate scope tested on 34 entries showed the considerable generality of the developed asymmetric transformation. A scale-up experiment and multiple enantioselective downstream transformations were also carried out, suggesting the prospective synthetic utility of the products.
Links
| MUNI/A/1393/2023, interní kód MU |
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