Syntheses and rearrangements of spirocyclic oxaziridines derived from unsymmetrical ketones

J Aube, M Hammond, E Gherardini…

文献索引：Aube, Jeffrey; Hammond, Marlys; Gherardini, Elyse; Takusagawa, Fusao Journal of Organic Chemistry, 1991 , vol. 56, # 18 p. 499 - 508

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被引用次数: 29

摘要

Oxaziridines provide useful alternatives to the Beckmann rearrangement and Schmidt reaction for ring enlargement of cyclic ketones. The procedure involves the condensation of the ketone in question with optically active a-methylbenzylamine, oxidation of the resultant imine, and photolysis to afford ring-expanded lactams. The a-phenylethyl substituent can be removed after photolysis to yield the N-unsubstituted lactam. When a distal ketone ...