An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application |
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| Authors: | Fengtian Xue |
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| Institution: | Department of Chemistry, Department of Biochemistry, Molecular Biology, and Cell Biology, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208-3113, USA |
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| Abstract: | We report a fast N→O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hydroxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state. |
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| Keywords: | N to O migration Boc group migration Intramolecular migration Cross-over experiment |
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