Stereoselective C-glycoside formation by a rhodium(I)-catalyzed 1,4-addition of arylboronic acids to acetylated enones derived from glycals.
[reaction: see text] A new method for the formation of C-glycosides has been developed employing a cationic rhodium(I)-catalyzed 1,4-addition of arylboronic acids to enones derived from glycals. The reaction is stereoselective for the alpha-anomer and is highly dependent on the nature of the rhodium catalyst.
Ramnauth
J
J
MCR Research Inc., Chemistry and Computer Sciences Bldg., York University, 4700 Keele St., Toronto, Ontario, Canada M3J 1P3.
Poulin
O
O
Bratovanov
S S
SS
Rakhit
S
S
Maddaford
S P
SP
D000107:Acetylation; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D001897:Boronic Acids; D006027:Glycosides; D007202:Indicators and Reagents; D012238:Rhodium