Iron-Catalyzed Stereoselective C–H Acylation of 2-Acetamido Acrylates

An iron-catalyzed oxidative acylation of acylamido acrylates with abundant aldehydes has been developed. The use of mono N-protected amino acids results in the unusual assembly of α,β-unsaturated compounds in a predictable (Z)-stereoselective fashion, thereby offering a complementary tool toward the...

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Detalles Bibliográficos
Autores: Kyriacou, Constantinos, Nguyen, Thanh V. Q., Czechtizky, Werngard, Gómez Bengoa, Enrique, Correa Navarro, Arkaitz
Tipo de recurso: artículo
Fecha de publicación:2025
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/74829
Acceso en línea:http://hdl.handle.net/10810/74829
Access Level:acceso abierto
Palabra clave:acylation
amino acid
cross-dehydrogenative coupling
dehydroalanine
C–H functionalization
Descripción
Sumario:An iron-catalyzed oxidative acylation of acylamido acrylates with abundant aldehydes has been developed. The use of mono N-protected amino acids results in the unusual assembly of α,β-unsaturated compounds in a predictable (Z)-stereoselective fashion, thereby offering a complementary tool toward the synthesis of unnatural γ-carbonyl α-amino acid derivatives. Density functional theory studies provide insights into the stereodetermining step of the radical reaction pathway