A hitherto unknown reactivity of a strained four-membered heterocycle, 1,2-oxazetidine, is reported. When reacted with organometallic compounds, this reagent provides electrophilic oxygen with a nitrogen-terminated two-carbon-atom tether. The synthetic versatility of the products obtained was demonstrated in various transformations, leading to efficient synthesis of six-, seven-, and eight-membered heterocyclic systems of pharmaceutical importance.
N-Protected 1,2-Oxazetidines as a Source of Electrophilic Oxygen: Straightforward Access to Benzomorpholines and Related Heterocycles by Using a Reactive Tether. -1,2-Oxazetidine reacts with organometallic compounds to provide electrophilic oxygen with a nitrogen-terminated two-carbon-atom tether. These products are converted to six-, seven-, and eight-membered heterocyclic systems which are of pharmaceutical importance. -(JAVORSKIS, T.; SRIUBAITE, S.; BAGDZIUNAS, G.; ORENTAS*, E.; Chem. -Eur. J. 21 (2015) 25, 9157-9164, http://dx.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.