Intramolecular nitrile oxide-alkene cycloaddition of sugar derivatives with unmasked hydroxyl group(s).
[reaction: see text] Intramolecular nitrile oxide-alkene cycloaddition (INOC) of sugar derivatives with one to four free hydroxyl group(s) is reported. The INOC reaction, using chloramine-T, in the presence of silica gel, to generate nitrile oxides from oximes, proceeded smoothly to afford five- or six-membered carbocycles in good to excellent yields. This new methodology alleviates protection/deprotection steps and makes the synthetic route shorter and more efficient.
Shing
Tony K M
TK
Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, NT, Hong Kong, China. tonyshing@cuhk.edu.hk
Wong
Wai F
WF
Cheng
Hau M
HM
Kwok
Wun S
WS
So
King H
KH
D000475:Alkenes / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002700:Chloramines / Q000737:chemistry; D003500:Cyclization; D006900:Hydroxylation; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010091:Oximes / Q000737:chemistry; D058428:Silica Gel; D012822:Silicon Dioxide / Q000737:chemistry; D014105:Tosyl Compounds / Q000737:chemistry
D000475:Alkenes; D002241:Carbohydrates; D002700:Chloramines; D007783:Lactones; D009570:Nitriles; D010091:Oximes; D014105:Tosyl Compounds; C016300:chloramine-T; D058428:Silica Gel; D012822:Silicon Dioxide