Stereoselective C-glycosidation of unprotected D-glycals with trimethylsilyl cyanide.
Unprotected glycals reacted with trimethylsilyl cyanide in the presence of a catalytic amount of a palladium compound to yield the 2,3-unsaturated glycosyl cyanides in high yield and in alpha-selectivity.
Hayashi
Masahiko
M
Department of Chemistry, Faculty of Science, Kobe University, Nada, Kobe, Japan. mhayashi@kobe-u.ac.jp
Kawabata
Hirotoshi
H
Nakayama
Shu-Zo
SZ
D003486:Cyanides / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D007202:Indicators and Reagents; D015394:Molecular Structure; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D003486:Cyanides; D006027:Glycosides; D007202:Indicators and Reagents; D014297:Trimethylsilyl Compounds; C058010:trimethylsilyl cyanide