ChemInform Abstract: Oxazolium-Derived Azomethine Ylides. External Oxazole Activation and Internal Dipole Trapping in the Synthesis of an Aziridinomitosene.
Abstract
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ChemInform Abstract
It is shown that benzylated aziridine derivatives of type (IV) can be selectively alkylated at the oxazole nitrogen yielding salts like (VI). Treatment of the latter with Bn-NMe3CN gives azomethine ylides [see (VII)] which undergo cycloaddition forming indoles like (VIII). Interestingly, under these conditions the aziridine ring remains intact. (VIII) can smoothly be transformed into the aziridinomitosene derivative (XI).