Synthesis and applications of a chiral-oxygenated 3-chloro-3,6-dihydro-2H-pyran obtained under Overman rearrangement conditions |
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Authors: | Ana Montero Esperanza Benito |
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Affiliation: | a Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain b The Scripps Research Institute, Department of Chemistry, La Jolla, CA 92037, USA |
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Abstract: | A chlorinated side product was formed under Overman rearrangement conditions from a trichloroacetimidate along with the expected allylic amide. The chlorinated product derived from a hex-2-enopyranoside was obtained in a totally stereoselective manner, and it can be a useful synthetic intermediate for chlorinated sugars. In order to improve the isolated yields of either the expected Overman rearrangement product or the chlorinated compound, we carried out a thorough study on the experimental conditions. The application of the latter for the synthesis of potential calpain inhibitors is also reported. |
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Keywords: | Chlorinated carbohydrate 3,6-Dihydro-2H-pyran Experimental modulation of the selectivity Overman rearrangement Peptide-carbohydrate hybrid Unsaturated sugar |
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