Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14160%2F24%3A00135761" target="_blank" >RIV/00216224:14160/24:00135761 - isvavai.cz</a>
Result on the web
<a href="https://pubs.acs.org/doi/10.1021/acs.orglett.4c00818?src=getftr" target="_blank" >https://pubs.acs.org/doi/10.1021/acs.orglett.4c00818?src=getftr</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.orglett.4c00818" target="_blank" >10.1021/acs.orglett.4c00818</a>
Alternative languages
Result language
angličtina
Original language name
Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
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Continuities
S - Specificky vyzkum na vysokych skolach
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organic Letters
ISSN
1523-7060
e-ISSN
1523-7052
Volume of the periodical
12
Issue of the periodical within the volume
26
Country of publishing house
US - UNITED STATES
Number of pages
6
Pages from-to
2505-2510
UT code for WoS article
001187658900001
EID of the result in the Scopus database
2-s2.0-85188239382