Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14160%2F24%3A00136923" target="_blank" >RIV/00216224:14160/24:00136923 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Result language
angličtina
Original language name
Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates
Original language description
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.
Czech name
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Czech description
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Project
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Continuities
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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