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@proceedings{2425138,
author = {Švestka, David and Bobáľ, Pavel and Waser, Mario and Otevřel, Jan},
booktitle = {ACS PUBLICATIONS SYMPOSIUM Catalysis for Organic Synthesis},
keywords = {Enantioselective organocatalysis; Takemoto catalyst; Formaldehyde},
language = {eng},
title = {Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates},
year = {2024}
}
TY - CONF
ID - 2425138
AU - Švestka, David - Bobáľ, Pavel - Waser, Mario - Otevřel, Jan
PY - 2024
TI - Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates
KW - Enantioselective organocatalysis
KW - Takemoto catalyst
KW - Formaldehyde
N2 - 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.
ER -
ŠVESTKA, David, Pavel BOBÁĽ, Mario WASER a Jan OTEVŘEL. Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates. In \textit{ACS PUBLICATIONS SYMPOSIUM Catalysis for Organic Synthesis}. 2024.
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