ORGN 491 |
| A novel, high-yielding method for sulfation of alcohols has been developed, proceeding via sulfite- and sulfate diester intermediates. In a convenient three-step procedure, involving (a) condensation of an alcohol with alkyl chlorosulfite, (b) oxidation and (c) nucleophilic disposition of alkyl substituent, a range of organic O-sulfates has been prepared, including di- and tetrasulfated compounds. Reactions are rapid and clean and the final products are obtained with excellent yields. It was found that the relative stability of the sulfite diesters –as O-sulfate precursors– allows introduction in an earlier stage of a synthetic sequence, thus providing synthetic flexibility that is difficult or impossible with anionic O-sulfates.
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
