TBHP promoted demethylation of α-amino carbonyl compounds: a concise approach to substituted γ-lactams?

Organic Chemistry Frontiers Pub Date: 2019-04-04 DOI: 10.1039/C9QO00103D

Abstract

A novel tert-butyl hydroperoxide (TBHP) promoted CH2-extrusion reaction of α-amino carbonyl compounds has been developed, which is driven by a demethylenation process to give various ring contraction products γ-lactams under radical conditions. The reaction shows good functional group tolerance and excellent chemo/regioselectivity; all the desired products are obtained in moderate to excellent yields.

Graphical abstract: TBHP promoted demethylation of α-amino carbonyl compounds: a concise approach to substituted γ-lactams
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