A Novel Synthesis of Densely Functionalized 3,4-β-Lactam Fused 1,4-Oxazepane via Tandem-7-exo-trig Intramolecular Oxa-Michael Reaction

Paniagua Armando Paniagua, Ram N. Yadav, Md Firoj Hossain, Ashok Kumar Srivastava, Bimal K. Banik

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

Resumen

Abstract: A versatile and chemoselective intramolecular oxa-Michael reaction of α,β-unsaturated ester tethered on a prebuilt stereodefined β-lactam ring in a novel synthesis of a bicyclic scaffold of 1,4-oxazepane embedded on the β-lactam ring has been developed. The tandem process involves a successive deprotection of the O-isopropylidene group, followed by the chemoselective nucleophilic conjugate addition of 2° hydroxy functionalities of vic diol to the unsaturated esters preferentially 7-exo-trig mode of ring closure. The developed protocol proceeded well under mild alkaline conditions and furnished a novel scaffold of bicyclic β-lactam featuring 1,4-oxazepane rings in a high chemoselective fashion.[Equation not available: see fulltext.]

Idioma originalInglés
Páginas (desde-hasta)117-124
Número de páginas8
PublicaciónMoscow University Chemistry Bulletin
Volumen77
N.º2
DOI
EstadoPublicada - abr 2022
Publicado de forma externa

Huella

Profundice en los temas de investigación de 'A Novel Synthesis of Densely Functionalized 3,4-β-Lactam Fused 1,4-Oxazepane via Tandem-7-exo-trig Intramolecular Oxa-Michael Reaction'. En conjunto forman una huella única.

Citar esto