Enantioselective N-Heterocyclic Carbene Catalyzed α-Oxidative Coupling of Enals with Carboxylic Acids Using an Iodine(III) Reagent.
Angew Chem Int Ed Engl
; 62(11): e202218362, 2023 Mar 06.
Article
em En
| MEDLINE
| ID: mdl-36651829
ABSTRACT
The enantioselective α-oxidative coupling of enals with carboxylic acids was developed via the umpolung of an NHC-bound enolate with an iodine(III) reagent. The corresponding α-acyloxyl-ß,γ-unsaturated esters were afforded in good yields, with high regio- and enantioselectivities. The key step of the reaction involves the formation of enol iodine(III) intermediate from the enolate with iodosobenzene, which changes the polarity of α-carbon of the enal from nucleophilic to electrophilic, and thus facilitates the subsequent addition of carboxylate.
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Coleções:
01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2023
Tipo de documento:
Article