TY - JOUR
T1 - Unusual regioselection in the Mitsunobu reactions of syn-2,3-dihydroxy esters
T2 - Synthesis of statine and its diastereomer
AU - Ko, Soo Y.
PY - 2002/4/19
Y1 - 2002/4/19
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0037134203&partnerID=8YFLogxK
U2 - 10.1021/jo015967f
DO - 10.1021/jo015967f
M3 - Article
C2 - 11950319
AN - SCOPUS:0037134203
SN - 0022-3263
VL - 67
SP - 2689
EP - 2691
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 8
ER -