Unprecedented highly stereoselective alpha- and beta-C-glycosidation with chiral titanium enolates.
[reaction: see text] Lewis acid mediated addition of chiral titanium enolates to glycals provides either alpha- or beta-1'-methyl-substituted C-glycosides. This highly stereoselective methodology permits the modular preparation of three of the four possible diastereomers.
Larrosa
Igor
I
Departament de Química Orgànica, Universitat de Barcelona, 08028 Barcelona, Catalonia, Spain.
Romea
Pedro
P
Urpí
Fèlix
F
Balsells
Daniel
D
Vilarrasa
Jaume
J
Font-Bardia
Mercè
M
Solans
Xavier
X
D006027:Glycosides; D007659:Ketones; D009005:Monosaccharides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014025:Titanium
C438934:C-glycoside; D006027:Glycosides; D007659:Ketones; D009005:Monosaccharides; D014025:Titanium