Publication: A short and convenient procedure for the stereoselective synthesis of 2-hydroxy-1-norbornanesulfonamides
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2004-01-26
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Elsevier Ltd.
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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.