TY - JOUR
T1 - Eu(OTf)3-Catalyzed highly regioselective nucleophilic ring opening of 2,3-epoxy alcohols
T2 - An efficient entry to 3-substituted 1,2-diol derivatives
AU - Uesugi, Shun Ichiro
AU - Watanabe, Tsubasa
AU - Imaizumi, Takamichi
AU - Shibuya, Masatoshi
AU - Kanoh, Naoki
AU - Iwabuchi, Yoshiharu
PY - 2014/9/5
Y1 - 2014/9/5
N2 - In our study of the total synthesis of (+)-irciniastatin A, we found a need to develop a method that enables a C3-selective nucleophilic ring opening of 2,3-epoxy alcohol by MeOH, by which we found that the use of combined catalytic amounts of Eu(OTf)3 and 2,6-di-tert-butyl-4-methylpyridine (DTBMP) enables the intended transformation to obtain 3-methoxy-1,2-diol efficiently. Promising features of a protocol that effects a highly regioselective nucleophilic ring opening of 2,3- and 3,4-epoxy alcohols using various nucleophiles including alcohols, thiols, and unprotected amines are described.
AB - In our study of the total synthesis of (+)-irciniastatin A, we found a need to develop a method that enables a C3-selective nucleophilic ring opening of 2,3-epoxy alcohol by MeOH, by which we found that the use of combined catalytic amounts of Eu(OTf)3 and 2,6-di-tert-butyl-4-methylpyridine (DTBMP) enables the intended transformation to obtain 3-methoxy-1,2-diol efficiently. Promising features of a protocol that effects a highly regioselective nucleophilic ring opening of 2,3- and 3,4-epoxy alcohols using various nucleophiles including alcohols, thiols, and unprotected amines are described.
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U2 - 10.1021/ol502264y
DO - 10.1021/ol502264y
M3 - Article
C2 - 25162733
AN - SCOPUS:84914166386
SN - 1523-7060
VL - 16
SP - 4408
EP - 4411
JO - Organic Letters
JF - Organic Letters
IS - 17
ER -