A versatile and straight chemoselective intramolecular oxy-Michael reaction of a b-unsaturated ester tethered on a prebuilt stereo defined b-lactam ring in a novel synthesis of a bicyclic scaffold of 1,4-oxazepane embedded on the b-lactam ring has been established. The tandem process involves a successive deprotection of the O-isopropylidene group, followed by the chemoselective nucleophilic conjugate addition of secondary 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 b-lactam featuring 1,4-oxazepane rings in a high chemoselective fashion.

Synthetic application of intramolecular aza-Michael reaction in the synthesis of 1,4-diazapane

ACS Spring Meeting 2021

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.