首页 | 本学科首页   官方微博 | 高级检索  
     


Intramolecular hydrogen abstraction promoted by N-radicals: synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems
Affiliation:1. Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México, D.F., Mexico;2. Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic;3. Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Palacký University & Institute of Experimental Botany ASCR, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic;1. Jhargram Raj College, Jhargram 721507, West Bengal, India;2. Central Inland Fisheries Research Institute, Barrackpore, Kolkata 700120, West Bengal, India;1. Department of Chemistry, Sapienza University of Rome, P.le A. Moro 5, 00185 Rome, Italy;2. Department of Physical Chemistry, Faculty of Science, University of Santiago de Compostela, Avda. Alfonso X El Sabio s/n, 27002 Lugo, Spain;3. Institute of Complex Systems (ISC) – CNR, UOS Sapienza, P.le Aldo Moro 2, 00185 Rome, Italy;4. Division of Physical Chemistry, Department of Chemistry, Center for Chemistry and Chemical Engineering, Lund University, SE-221 00 Lund, Sweden;1. Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México, D.F., Mexico;2. Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic
Abstract:Homochiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems can be synthesized by reaction of specifically protected phosphoramidate derivatives of carbohydrates with (diacetoxyiodo)benzene or iodosylbenzene and iodine. The reaction mechanism goes through homolytic fragmentation of a hypothetical iodoamide intermediate. The N-radicals so generated participate in an intramolecular hydrogen abstraction reaction (IHA) to give the aforementioned bicycles.
Keywords:
本文献已被 ScienceDirect 等数据库收录!
设为首页 | 免责声明 | 关于勤云 | 加入收藏

Copyright©北京勤云科技发展有限公司  京ICP备09084417号