TY - JOUR
T1 - A novel pentose synthesis via palladium(II)-catalyzed cyclization of an unstable hemiacetal
AU - Awasaguchi, Ken Ichiro
AU - Miyazawa, Masahiro
AU - Uoya, Ikuyo
AU - Inoue, Koichi
AU - Nakamura, Koji
AU - Yokoyama, Hajime
AU - Hirai, Yoshiro
PY - 2010
Y1 - 2010
N2 - PdCl2(PhCN)2 (5 mol%)-catalyzed cyclization of a hemiacetal derived from (E,2S,3R)-2,3-isopropylidenedioxy-6-(tetrahydro-2H- pyran-2-yl)-4-hexenal and methanol gave substituted furanoside in moderate yield, exclusively via 5-exo-mode cyclization, without the need for a reoxidant. New stereogenic centers at C1 and C4 on the tetrahydrofuran ring showed preferential 1R and 4R stereochemistry due to anomeric effect (n oσ*c-o) and A1,2 strain, respectively. This methodology was applied to stereocontrolled synthesis of pentoses: D-ribose and L-lyxose.
AB - PdCl2(PhCN)2 (5 mol%)-catalyzed cyclization of a hemiacetal derived from (E,2S,3R)-2,3-isopropylidenedioxy-6-(tetrahydro-2H- pyran-2-yl)-4-hexenal and methanol gave substituted furanoside in moderate yield, exclusively via 5-exo-mode cyclization, without the need for a reoxidant. New stereogenic centers at C1 and C4 on the tetrahydrofuran ring showed preferential 1R and 4R stereochemistry due to anomeric effect (n oσ*c-o) and A1,2 strain, respectively. This methodology was applied to stereocontrolled synthesis of pentoses: D-ribose and L-lyxose.
UR - http://www.scopus.com/inward/record.url?scp=79751479069&partnerID=8YFLogxK
U2 - 10.3987/COM-10-12001
DO - 10.3987/COM-10-12001
M3 - 学術論文
AN - SCOPUS:79751479069
SN - 0385-5414
VL - 81
SP - 2105
EP - 2121
JO - Heterocycles
JF - Heterocycles
IS - 9
ER -