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Updated: Jul 17, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Preparation and reactivity of versatile alpha-amino ketones
Lily Yu1, Akos Kokai, Andrei K Yudin
1Davenport Research Laboratories, Department of Chemistry, The University of Toronto, 80 St. George Street, Toronto, Canada, M5S 3H6.
Abstract:
Many challenges of chemoselectivity arise from the requirement to manipulate incompatible functional groups. Synthetic methods that do not rely on protecting groups are of strategic significance to chemical synthesis. Particularly valuable are molecules with reactive functionalities that are kinetically stabilized against inter- or intramolecular reactions with each other. We have developed a simple access to molecules that contain both ketone and N-H aziridine functionalities. These compounds were found to undergo highly selective reduction and carbonyl addition reactions, making them versatile precursors to complex amines.
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