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Mild and selective ring-cleavage of cyclic carbamates to amino alcohols
Affiliation:1. From the Department of Neurosurgery, First Affiliated Hospital of Sun Yat-sen University, Guangzhou China;2. Department of Neurosurgery, Sun Yat-sen University Cancer Center, State Key Laboratory of Oncology in South China; Collaborative Innovation Center for Cancer Medicine, Guangzhou China;3. Department of Cardiology, First Affiliated Hospital of Sun Yat-sen University, Guangzhou, China;4. Department of Cardiology, Liuzhou Municipal Liutie Central Hospital, Liuzhou, China;5. Department of Ultrasound Imaging, First Affiliated Hospital of Sun Yat-sen University, Guangzhou, China;6. Department of Histology and Embryology, Zhongshan School of Medicine, Sun Yat-sen University, Guangzhou, China;7. Department of Stem Cell Biology and Regenerative Medicine, Cleveland Clinic, Lerner Research Institute, Cleveland, Ohio.
Abstract:N-tert-Butoxycarbonylated 2-oxazolidinones and tetrahydro-2-oxazinones are smoothly cleaved to acyclic N-Boc-amino alcohols on treatment with catalytic amounts of cesium carbonate at room temperature. The versatility of the procedure is demonstrated in a facile cleavage of highly functionalized heterocycles without epimerization and β-elimination.
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