Formation and reactivity of novel pyranosidic nicholas oxocarbenium ions: access to C-ketosides and branched-chain C-ketosides.
[Structure: see text] Dicobalt hexacarbonyl propargyl complexes, prepared from alkynyl ketoses, display an unexpected reactivity when treated with Lewis acids in the presence of nucleophiles and furnish C-ketosides, branched-chain C-ketosides, or branched-chain C-glycals depending on the nucleophile and the carbohydrate starting material.
Gómez
Ana M
AM
Instituto de Química Organica General (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain. anago@iqog.csic.es
Uriel
Clara
C
Valverde
Serafín
S
López
J Cristóbal
JC
D002241:Carbohydrates / Q000737:chemistry; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D002241:Carbohydrates; D006027:Glycosides; D009942:Organometallic Compounds; D003035:Cobalt