Pentaenolate activation in the organocatalytic allylic alkylation of indene-2-carbaldehydes.

Molecular Structure Allyl Compounds Stereoisomerism Alkylation Carbonates

Journal

Chemical communications (Cambridge, England)
ISSN: 1364-548X
Titre abrégé: Chem Commun (Camb)
Pays: England
ID NLM: 9610838

Informations de publication

Date de publication:
15 Jun 2023
Historique:
medline: 1 6 2023
pubmed: 1 6 2023
entrez: 1 6 2023
Statut: epublish

Résumé

In this manuscript, the application of pentaenolate intermediates in the allylic alkylation of indene-2-carbaldehydes with Morita-Baylis-Hillman (MBH) carbonates is described. The reaction has been carried out in a highly enantio- and diastereoselective manner due to the use of a chiral tertiary amine as a nucleophilic catalyst. The developed reactivity constitutes the first application of organocatalytic pentaenolate activation in asymmetric synthesis, expanding the arsenal of catalytic methods.

Identifiants

DOI: 10.1039/d3cc00900a PMID: 37259939
pubmed: 37259939
doi: 10.1039/d3cc00900a
doi:

Substances chimiques

Allyl Compounds 0
Carbonates 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

7655-7658

Auteurs

Adam Cieśliński (A)

Institute of Organic Chemistry, Faculty of Chemistry Lodz University of Technology Żeromskiego 116, Łódź 90-924, Poland. lukasz.albrecht@p.lodz.pl.

Sebastian Frankowski (S)

Institute of Organic Chemistry, Faculty of Chemistry Lodz University of Technology Żeromskiego 116, Łódź 90-924, Poland. lukasz.albrecht@p.lodz.pl.

Łukasz Albrecht (Ł)

Institute of Organic Chemistry, Faculty of Chemistry Lodz University of Technology Żeromskiego 116, Łódź 90-924, Poland. lukasz.albrecht@p.lodz.pl.
ORCID: 0000-0002-4669-7670

Articles similaires

Use of dislodgeable foliar residue studies for the evaluation of isomerization potential of active substances for non-dietary risk assessment.

Silke Wagner, Christian J Kuster
1.00
Risk Assessment Plant Leaves Isomerism Humans Stereoisomerism

Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di-

Alonzo González-González, Oscar Sánchez-Sánchez, Lilián Yépez-Mulia et al.
1.00
Giardia lamblia Trichomonas vaginalis Entamoeba histolytica Antiprotozoal Agents Quinoxalines

Preparation of D-NCCDs and its application in fluorescent/colorimetric dual-mode discrimination of glutamine enantiomers.

Xuan Liao, Cancan Lu, Yaning Duan et al.
1.00
Glutamine Stereoisomerism Spectrometry, Fluorescence Colorimetry Carbon

From loose sand to sandstone: An experimental approach on early calcite precipitation in sands of siliciclastic and mixed carbonate-siliciclastic composition.

Meike Janssen, Luca Caracciolo, Linda M Bonnell et al.
1.00
Calcium Carbonate Chemical Precipitation Sand Microscopy, Electron, Scanning Carbonates

Classifications MeSH

questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Pentaenolate activation in the organocatalytic...
questionsmedicales.fr › Composés chimiques organiques › Hydrocarbures › Hydrocarbures acycliques › Alcènes › Composés allyliques › Pentaenolate activation in the organocatalytic...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes de chimie organique › Isomérie › Stéréoisomérie › Pentaenolate activation in the organocatalytic...
questionsmedicales.fr › Métabolisme › Alkylation › Pentaenolate activation in the organocatalytic...
questionsmedicales.fr › Produits chimiques inorganiques › Électrolytes › Ions › Anions › Carbonates › Pentaenolate activation in the organocatalytic...