ol050044i_si_001.pdf (395.78 kB)
De Novo Enantioselective Syntheses of Galacto-Sugars and Deoxy Sugars via the Iterative Dihydroxylation of Dienoate
journal contribution
posted on 2005-02-17, 00:00 authored by Md. Moinuddin Ahmed, Bryan P. Berry, Thomas J. Hunter, Dennis J. Tomcik, George A. O'DohertyAn 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.