2024
Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates
ŠVESTKA, David; Pavel BOBÁĽ; Mario WASER a Jan OTEVŘELZákladní údaje
Originální název
Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates
Autoři
Vydání
ACS PUBLICATIONS SYMPOSIUM Catalysis for Organic Synthesis, 2024
Další údaje
Jazyk
angličtina
Typ výsledku
Prezentace na konferencích
Obor
30104 Pharmacology and pharmacy
Stát vydavatele
Česká republika
Utajení
není předmětem státního či obchodního tajemství
Označené pro přenos do RIV
Ano
Kód RIV
RIV/00216224:14160/24:00136923
Organizační jednotka
Farmaceutická fakulta
Klíčová slova anglicky
Enantioselective organocatalysis; Takemoto catalyst; Formaldehyde
Příznaky
Mezinárodní význam
Změněno: 25. 8. 2024 22:41, Mgr. David Švestka, Ph.D.
Anotace
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.
Návaznosti
| MUNI/A/1393/2023, interní kód MU |
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