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

Article in a journal

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

is not subject to a state or trade secret

References:

URL

Impact factor

Impact factor: 5.000

RIV identification code

RIV/00216224:14160/24:00135761

Organization unit

Faculty of Pharmacy

DOI

https://doi.org/10.1021/acs.orglett.4c00818

UT WoS

001187658900001

EID Scopus

2-s2.0-85188239382

Keywords in English

ALDOL REACTIONENANTIOSELECTIVE HYDROXYMETHYLATIONALPHA-HYDROXYMETHYLATIONOXINDOLESALDEHYDESCHEMISTRYTOOL

Abstract

In the original language

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

MUNI/IGA/0916/2021, interní kód MU

Name: Asymmetric organocatalyzed hydroxymethylation of isoindolinones

Investor: Masaryk University

90242, large research infrastructures

Name: CIISB III

Cite

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://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 = {https://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://doi.org/10.1021/acs.orglett.4c00818.

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