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A short and convenient procedure for the stereoselective synthesis of 2-hydroxy-1-norbornanesulfonamides
Institution:1. Dpto. de Quı́mica Orgánica I, Fac. de CC. Quı́micas, Universidad Complutense de Madrid, Ciudad Universitaria, 28040 Madrid, Spain;2. Dpto. de Quı́mica Orgánica y Biologı́a, Fac. de Ciencias, Cuidad Universitaria, UNED, Senda del Rey 9, 28040 Madrid, Spain;1. Department of Chemistry, Purdue University, West Lafayette, IN 47907, United States;2. Department of Medicinal Chemistry, Purdue University, West Lafayette, IN 47907, United States;3. Department of Biochemistry, Purdue University, West Lafayette, IN 47907, United States;4. Department of Biological Sciences, Purdue University, West Lafayette, IN 47907, United States;5. Protein Studies Program, Oklahoma Medical Research Foundation, United States;6. Department of Biochemistry and Molecular Biology, University of Oklahoma Health Science Center, Oklahoma City, OK 73104, United States;1. Enamine Ltd, Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine;2. Department of Chemistry, Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, 01033 Kyiv, Ukraine
Abstract:A short and convenient procedure for the stereoselective synthesis of novel optically active 2-hydroxy-1-norbornanesulfonamides starting from commercially available natural camphor and fenchone is reported. The synthetic route involves a nucleophilic substitution at the sulfenyl sulfur atom of 2-methylene-1-norbornylthiotriflates followed by oxidation of the intermediate sulfenamides and highly diastereoselective reduction of the carbonyl group of the parent 2-oxo-1-norbornanesulfonamides.
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