Publication | Open Access
Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff–Staudinger Cascade Reaction
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2016
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Single-mode Bench-top ResonatorEngineeringEnabling TechnologiesOrganic ChemistryWolff–staudinger Cascade ReactionCatalysisStereoselective SynthesisChemistryMolecular EngineeringHigh TemperatureMicrowave SynthesisMicrowave-assisted Flow GenerationBiophysics
A new, single-mode bench-top resonator was evaluated for the microwave-assisted flow generation of primary ketenes by thermal decomposition of α-diazoketones at high temperature. A number of amides and β-lactams were obtained by ketene generation <i>in situ</i> and reaction with amines and imines, respectively, in good to excellent yields. The preferential formation of <i>trans</i>-configured β-lactams was observed during the [2+2] Staudinger cycloaddition of a range of ketenes with different imines under controlled reaction conditions. Some insights into the mechanism of this reaction at high temperature are reported, and a new web-based molecular viewer, which takes advantage from Augmented Reality (AR) technology, is also described for a faster interpretation of computed data.