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Synthesis of Tertiary Amines through Extrusive Alkylation of Carbamates
Guoliang Zhang1, David Favela1, Winston L Chow1
1Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, United States.
Abstract:
Basic amines are key elements of many biologically active natural products and pharmaceuticals. Given their inherent reactivity, it is often necessary to protect basic amines during target-directed synthesis, which results in wasteful protection/deprotection sequences. We report a step-economical approach enabling the protection of secondary amines as carbamates prior to their conversion to tertiary amines via the formal extrusion of CO2. This method is applied to the synthesis of iboga alkaloids (±)-conodusine A and (±)-conodusine B.
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