De novo enantioselective syntheses of galacto-sugars and deoxy sugars via the iterative dihydroxylation of dienoate |
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Authors: | Ahmed Md Moinuddin Berry Bryan P Hunter Thomas J Tomcik Dennis J O'Doherty George A |
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Affiliation: | Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA. |
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Abstract: | An efficient route to various sugar lactones has been developed. Key to the overall transformation is the sequential osmium-catalyzed dihydroxylation of 2,4-dienoates. The simplest (one-step/racemic) example of this reaction occurs when the dihydroxylation is performed with aqueous NMO in MeOH. When the first dihydroxylation is performed using the AD-mix procedure, an enantioselective variant results. When a matched AD-mix procedure is used for the second dihydroxylation, an exceedingly diastereo- and enantioselective synthesis of galacto-1,4-lactone results. [Reaction: see text] |
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