Catalysis; Chemical reactions; Crystallography; Molecular structure; Nitrogen compounds; Olefins; Organic compounds; Stereoselectivity; Thermogravimetric analysis; Carbenes; Organocatalysis; Reaction mechanism; X ray crystallography
Abstract :
[en] The reaction of ethylphenylketene with 1,3-dimesitylimidazol-2-ylidene (IMes) or 1,3-dimesitylimidazolin-2-ylidene (SIMes) afforded the corresponding azolium enolates in high yields. The two zwitterions were fully characterized by various analytical techniques. Their thermal stabilities were monitored by thermogravimetric analysis and the molecular structure of SIMes.EtPhC=C=O was determined by means of X-ray crystallography. A mechanism was proposed to account for the trans-diastereoselectivity observed in the [2+2] cycloaddition of ketenes and N-protected imines catalyzed by N-heterocyclic carbenes and an extensive catalytic screening was performed to test its validity. The steric bulk of the NHC catalyst markedly affected the cis/trans ratio of the model β-lactam product. The nature of the solvent used to carry out the Staudinger reaction also significantly influenced its diastereoselectivity. Conversely, the nature of the substituent on the N-sulfonated imine reagent and the reaction temperature were less critical parameters.
Disciplines :
Chemistry
Author, co-author :
Hans, Morgan ; Université de Liège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique
Wouters, Johan; Department of Chemistry, Université de Namur, 61 Rue de Bruxelles, Namur, Belgium
Demonceau, Albert ; Université de Liège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique
Delaude, Lionel ; Université de Liège > Département de chimie (sciences) > Chimie organométallique et catalyse homogène
Language :
English
Title :
Probing the Diastereoselectivity of Staudinger Reactions Catalyzed by N-Heterocyclic Carbenes
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