- N-protected 1,2-oxazetidines as a source of electrophilic oxygen: Straightforward access to benzomorpholines and related heterocycles by using a reactive tether
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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).
- Javorskis, Tomas,Sriubaite, Simona,Bagd?iunas, Gintautas,Orentas, Edvinas
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p. 9157 - 9164
(2015/06/16)
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- Hg cathode-free electrochemical detosylation of N,N-disubstituted p-toluenesulfonamides: mild, efficient, and selective removal of N-tosyl group
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Hg cathode-free electrochemical detosylation of N,N-disubstituted p-toluenesulfonamides was successfully carried out by a constant current electrolysis using an undivided cell equipped with a platinum cathode and a magnesium anode in the presence of an arene mediator. The deprotection proceeded efficiently and selectively under neutral and mild conditions with a stoichiometric amount of electricity without the use of an Hg cathode to obtain the corresponding secondary amines in good to excellent yields.
- Senboku, Hisanori,Nakahara, Kazuo,Fukuhara, Tsuyoshi,Hara, Shoji
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supporting information; experimental part
p. 435 - 438
(2010/03/04)
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