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New Stereoselective β-C-Glycosidation by Uncatalyzed 1,4-Addition of Organolithium Reagents to a Glycal-Derived Vinyl Oxirane

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journal contribution
posted on 16.05.2003, 00:00 by Valeria Di Bussolo, Micaela Caselli, Mauro Pineschi, Paolo Crotti
Epoxide 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.