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Unusual regioselection in the Mitsunobu reactions of syn-2,3-dihydroxy esters: Synthesis of statine and its diastereomer
- Unusual regioselection in the Mitsunobu reactions of syn-2,3-dihydroxy esters: Synthesis of statine and its diastereomer
- Ko S.Y.
- Ewha Authors
- SCOPUS Author ID
- Issue Date
- Journal Title
- Journal of Organic Chemistry
- vol. 67, no. 8, pp. 2689 - 2691
- SCI; SCIE; SCOPUS
- Mitsunobu reactions of syn-2,3-dihydroxy esters exhibit a complete regioselection for the β-hydroxyl group. Benzoylation, azidation, and tosylation have been performed under these conditions. β-Functionalizations of syn-2,3-dihydroxy esters are uncommon, and the Mitsunobu reactions are complementary to other diol chemistries in the regioselection. In addition, the configurational inversion accompanying the Mitsunobu protocol offers a means for diastereochemical diversity, as exemplified by a synthesis of statine and its anti diastereomer. These findings will further expand the synthetic utilities of the Sharpless AD process.
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