Preparation and reactivity of versatile alpha-amino ketones.
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.
Yu
Lily
L
Davenport Research Laboratories, Department of Chemistry, The University of Toronto, 80 St. George Street, Toronto, Canada, M5S 3H6.
Kokai
Akos
A
Yudin
Andrei K
AK
D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry; D002614:Chelating Agents / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D009942:Organometallic Compounds / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D000588:Amines; D001388:Aziridines; D002614:Chelating Agents; D004952:Esters; D007202:Indicators and Reagents; D007659:Ketones; D009942:Organometallic Compounds