Unusual regioselection in the Mitsunobu reactions of syn-2,3-dihydroxy esters: synthesis of statine and its diastereomer.
Mitsunobu reactions of syn-2,3-dihydroxy esters exhibit a complete regioselection for the beta-hydroxyl group. Benzoylation, azidation, and tosylation have been performed under these conditions. Beta-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.
Ko
Soo Y
SY
Department of Chemistry and Division of Molecular and Life Sciences, Ewha Womans University, Seoul 120-750, Korea. sooyko@mm.ewha.ac.kr
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D004952:Esters; C013165:statine