Continuous-flow synthesis of 2H-azirines and their diastereoselective transformation to aziridines
Marcus Baumann *, Ian R. Baxendale
- Department of Chemistry, University of Durham, South Road, Durham, DH1 3LE, UKRead the publication that featured this abstract
Using continuous-flow techniques, a small collection of 2H-azirines was prepared from oxime precursors via mesylation and base-promoted cyclisation. The 2H-azirines were either isolated after in-line purification or derivatised into a selection of 2-substituted aziridines through a telescoped reaction sequence involving nitrile, trifluoromethyl, or hydride nucleophilic addition. Importantly, these 2-substituted aziridines were produced with high cis diastereoselectivity providing access to small chiral heterocyclic entities that hold promise for medicinal chemistry programs because of their druglike features.
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