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Unusual regioselection in the Mitsunobu reactions of syn-2,3-dihydroxy esters: Synthesis of statine and its diastereomer

Title
Unusual regioselection in the Mitsunobu reactions of syn-2,3-dihydroxy esters: Synthesis of statine and its diastereomer
Authors
Ko S.Y.
Ewha Authors
고수영
SCOPUS Author ID
고수영scopus
Issue Date
2002
Journal Title
Journal of Organic Chemistry
ISSN
0022-3263JCR Link
Citation
vol. 67, no. 8, pp. 2689 - 2691
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
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.
DOI
10.1021/jo015967f
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자연과학대학 > 화학·나노과학전공 > Journal papers
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