Oxazolium-derived azomethine ylides. External oxazole activation and internal dipole trapping in the synthesis of an aziridinomitosene

E Vedejs, DW Piotrowski, FC Tucci

文献索引：Vedejs; Klapars; Naidu; Piotrowski; Tucci Journal of the American Chemical Society, 2000 , vol. 122, # 22 p. 5401 - 5402

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被引用次数: 61

摘要

Intermolecular alkylation of the aziridinyl oxazole 20 using PhSO2CH2CH2OTf is possible despite the presence of potentially nucleophilic aziridine nitrogen. The resulting oxazolium salt 22 reacts with BnNMe3 (+) CN (-) to produce the azomethine ylide 24b via electrocyclic ring opening of an oxazoline 23b. Internal cycloaddition affords 26 in 66% yield. After saponification and base-induced cleavage of the N-phenylsulfonylethyl group, ...