Asymmetric Organocatalyzed Transfer Hydroxymethylation of
Isoindolinones Using Formaldehyde Surrogates

J 2024

Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates

ŠVESTKA, David, Pavel BOBÁĽ, Jan OTEVŘEL a Mario WASER

Základní údaje

Originální název

Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates

Autoři

ŠVESTKA, David (203 Česká republika, domácí), Pavel BOBÁĽ (703 Slovensko, domácí), Jan OTEVŘEL (203 Česká republika, domácí) a Mario WASER (40 Rakousko)

Vydání

Organic Letters, Spojené státy, American Chemical Society, 2024, 1523-7060

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 5.200 v roce 2022

Organizační jednotka

Farmaceutická fakulta

DOI

http://dx.doi.org/10.1021/acs.orglett.4c00818

UT WoS

001187658900001

Klíčová slova anglicky

ALDOL REACTIONENANTIOSELECTIVE HYDROXYMETHYLATIONALPHA-HYDROXYMETHYLATIONOXINDOLESALDEHYDESCHEMISTRYTOOL

Štítky

rivok, ÚChL

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 20. 5. 2024 14:31, Mgr. Daniela Černá

Anotace

V originále

The piperidine-based Takemoto catalyst has been successfully employed in a novel asymmetric transfer hydroxymethylation of activated isoindolinones, allowing us to prepare the enantioenriched hydroxymethylated adducts in good to excellent yields (48–96%) and enantiopurities (81:19–97:3 e.r.). To increase the reaction rate without compromising the selectivity, carefully optimized formaldehyde surrogates were employed, providing a convenient source of anhydrous formaldehyde with a base-triggered release. The substrate scope, including 34 entries, showed the considerable generality of the asymmetric transformation, and most entries exhibited complete conversions in 24–48 h. A scale-up experiment and multiple enantioselective downstream transformations were also carried out, suggesting the prospective synthetic utility of the products.

Návaznosti

LM2023042, projekt VaV

Název: Česká infrastruktura pro integrativní strukturní biologii

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, CIISB - Česká infrastruktura pro integrativní strukturní biologii

MUNI/IGA/0916/2021, interní kód MU

Název: Asymmetric organocatalyzed hydroxymethylation of isoindolinones

Investor: Masarykova univerzita, Asymmetric organocatalyzed hydroxymethylation of isoindolinones

Citovat

ŠVESTKA, David, Pavel BOBÁĽ, Jan OTEVŘEL a Mario WASER. Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates. Organic Letters. Spojené státy: American Chemical Society, 2024, roč. 12, č. 26, s. 2505-2510. ISSN 1523-7060. Dostupné z: https://dx.doi.org/10.1021/acs.orglett.4c00818.

@article{2390978,
   author = {Švestka, David and Bobáľ, Pavel and Otevřel, Jan and Waser, Mario},
   article_location = {Spojené státy},
   article_number = {26},
   doi = {http://dx.doi.org/10.1021/acs.orglett.4c00818},
   keywords = {ALDOL REACTIONENANTIOSELECTIVE HYDROXYMETHYLATIONALPHA-HYDROXYMETHYLATIONOXINDOLESALDEHYDESCHEMISTRYTOOL},
   language = {eng},
   issn = {1523-7060},
   journal = {Organic Letters},
   title = {Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates},
   url = {https://pubs.acs.org/doi/10.1021/acs.orglett.4c00818?src=getftr},
   volume = {12},
   year = {2024}
}

TY  - JOUR
ID  - 2390978
AU  - Švestka, David - Bobáľ, Pavel - Otevřel, Jan - Waser, Mario
PY  - 2024
TI  - Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates
JF  - Organic Letters
VL  - 12
IS  - 26
SP  - 2505-2510
EP  - 2505-2510
PB  - American Chemical Society
SN  - 15237060
KW  - ALDOL REACTIONENANTIOSELECTIVE HYDROXYMETHYLATIONALPHA-HYDROXYMETHYLATIONOXINDOLESALDEHYDESCHEMISTRYTOOL
UR  - https://pubs.acs.org/doi/10.1021/acs.orglett.4c00818?src=getftr
N2  - The piperidine-based Takemoto catalyst has been successfully employed in a novel asymmetric transfer hydroxymethylation of activated isoindolinones, allowing us to prepare the enantioenriched hydroxymethylated adducts in good to excellent yields (48–96%) and enantiopurities (81:19–97:3 e.r.). To increase the reaction rate without compromising the selectivity, carefully optimized formaldehyde surrogates were employed, providing a convenient source of anhydrous formaldehyde with a base-triggered release. The substrate scope, including 34 entries, showed the considerable generality of the asymmetric transformation, and most entries exhibited complete conversions in 24–48 h. 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, Jan OTEVŘEL a Mario WASER. Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates. \textit{Organic Letters}. Spojené státy: American Chemical Society, 2024, roč.~12, č.~26, s.~2505-2510. ISSN~1523-7060. Dostupné z: https://dx.doi.org/10.1021/acs.orglett.4c00818.

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