Four O-perbenzylated glycosyl cyanides were converted by treatment with BrCH2CO2Et/Zn in THF at reflux (Blaise-Kishi reaction) into the corresponding C-glycosyl beta-enamino esters which in turn were reduced by NaBH(OAc)3 to give four pairs of C-glycosyl (R)- and (S)-beta-amino esters.
A facile and general entry to C-glycosyl (R)- and (S)-beta-amino acid pairs from glycosyl cyanides through enamino ester intermediates
DONDONI, Alessandro;MASSI, Alessandro;
2006
Abstract
Four O-perbenzylated glycosyl cyanides were converted by treatment with BrCH2CO2Et/Zn in THF at reflux (Blaise-Kishi reaction) into the corresponding C-glycosyl beta-enamino esters which in turn were reduced by NaBH(OAc)3 to give four pairs of C-glycosyl (R)- and (S)-beta-amino esters.File in questo prodotto:
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