438013-84-4Relevant articles and documents
N-protected 1,2-oxazetidines as a source of electrophilic oxygen: Straightforward access to benzomorpholines and related heterocycles by using a reactive tether
Javorskis, Tomas,Sriubaite, Simona,Bagd?iunas, Gintautas,Orentas, Edvinas
, p. 9157 - 9164 (2015/06/16)
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. Open and then close: The O-selective ring-opening reaction of 1,2-oxazetidines with organometallic compounds provides tethered phenol derivatives that can be used to access six-, seven-, and eight-membered heterocyclic systems in only a few steps (see scheme; Ts=tosyl).
