ol034662f_si_001.pdf (102.44 kB)
New Stereoselective β-C-Glycosidation by Uncatalyzed 1,4-Addition of Organolithium Reagents to a Glycal-Derived Vinyl Oxirane
journal contribution
posted on 2003-05-16, 00:00 authored by Valeria Di Bussolo, Micaela Caselli, Mauro Pineschi, Paolo CrottiEpoxide 4 is generated in situ from d-glucal-derived hydroxy mesylate 3. Reaction of epoxide 4 with a series of alkyl- and aryllithium reagents
affords 2,3-unsaturated β-C-glycosides with excellent 1,4-regioselectivity and complete stereoselectivity for the β-glycoside. Other organometallic
reagents demonstrate more complex behavior in their reactions with epoxide 4.