TY - JOUR
T1 - [1,2]-Wittig rearrangement of acetal systems
T2 - A highly stereocontrolled conversion of O-glycosides to C-glycosides
AU - Tomooka, K.
AU - Yamamoto, H.
AU - Nakai, T.
PY - 1996/4/3
Y1 - 1996/4/3
N2 - We envisioned that acetal systems such as O-glycosides would undergo the [1,2]-Wittig shift with great facility owing to the relatively large stability of the α-oxy radical, together with retention of the anomeric configuration. We now wish to report that the [1,2]-Wittig rearrangement of O-glycosides proceeds with efficient stereocontrol over both the anomeric center and the new chiral center formed on the side chain to give the stereo-defined C-glycosides in high yields. We have demonstrated that the [1,2]-Wittig rearrangement of O-glycosides proceeds with efficient stereocontrol over both the anomeric center and the side-chain chiral center to give a novel class of the stereo-defined C-glycosides which is otherwise difficult to obtain.
AB - We envisioned that acetal systems such as O-glycosides would undergo the [1,2]-Wittig shift with great facility owing to the relatively large stability of the α-oxy radical, together with retention of the anomeric configuration. We now wish to report that the [1,2]-Wittig rearrangement of O-glycosides proceeds with efficient stereocontrol over both the anomeric center and the new chiral center formed on the side chain to give the stereo-defined C-glycosides in high yields. We have demonstrated that the [1,2]-Wittig rearrangement of O-glycosides proceeds with efficient stereocontrol over both the anomeric center and the side-chain chiral center to give a novel class of the stereo-defined C-glycosides which is otherwise difficult to obtain.
UR - http://www.scopus.com/inward/record.url?scp=0030567340&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0030567340&partnerID=8YFLogxK
U2 - 10.1021/ja953933h
DO - 10.1021/ja953933h
M3 - Article
AN - SCOPUS:0030567340
VL - 118
SP - 3317
EP - 3318
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 13
ER -