Synthesis of alkyl and aryl C-pyranosides using organozinc reagents via a Ferrier-type rearrangement.
The reaction of 1,2-dihydropyranyl acetates with dimethylzinc, diethylzinc and diphenylzinc in the presence of CF3COOH gave the corresponding alky and aryl C-pyranosides via a Ferrier rearrangement in excellent yields. Use of the organozinc species, CF3CO2ZnPh, reacted with high stereoselectivity to give the phenyl C-glycosides. Arylzinc chlorides could also be successfully applied to this reaction in the presence of BF3.OEt2.
Xue
Song
S
Department of Chemistry, University of Science and Technology of China, Hefei 230026, PR China. xuesong@ustc.edu.cn
He
Lin
L
Han
Kai-Zhen
KZ
Zheng
Xiao-Qi
XQ
Guo
Qing-Xiang
QX
D000473:Alkanes / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D017967:Zinc Compounds / Q000737:chemistry*
D000473:Alkanes; D009942:Organometallic Compounds; D011714:Pyrans; D017967:Zinc Compounds