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 and Mario WASER

Basic 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), Jan OTEVŘEL (203 Czech Republic, belonging to the institution) and Mario WASER (40 Austria)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 5.200 in 2022

Organization unit

Faculty of Pharmacy

DOI

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

UT WoS

001187658900001

Keywords in English

ALDOL REACTIONENANTIOSELECTIVE HYDROXYMETHYLATIONALPHA-HYDROXYMETHYLATIONOXINDOLESALDEHYDESCHEMISTRYTOOL

Abstract

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.

Links

LM2023042, research and development project

Name: Česká infrastruktura pro integrativní strukturní biologii

Investor: Ministry of Education, Youth and Sports of the CR, CIISB - Czech Infrastructure for Integrative Structural Biology

MUNI/IGA/0916/2021, interní kód MU

Name: Asymmetric organocatalyzed hydroxymethylation of isoindolinones

Investor: Masaryk University

Citovat

ŠVESTKA, David, Pavel BOBÁĽ, Jan OTEVŘEL and Mario WASER. Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates. Organic Letters. Spojené státy: American Chemical Society, 2024, vol. 12, No 26, p. 2505-2510. ISSN 1523-7060. Available from: 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 and Mario WASER. Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates. \textit{Organic Letters}. Spojené státy: American Chemical Society, 2024, vol.~12, No~26, p.~2505-2510. ISSN~1523-7060. Available from: https://dx.doi.org/10.1021/acs.orglett.4c00818.

Detailed Information on Publication Record