[GRAPHICS] 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 beta-C-glycosides with excellent 1,4-regioselectivity and complete stereoselectivity for the beta-glycoside. Other organometallic reagents demonstrate more complex behavior in their reactions with epoxide 4.
New Stereoselective beta-C-glycosidation by Uncatalized 1,4-Addition of Organolithium Reagents to a Glycal-derived Vinyl Oxirane
DI BUSSOLO, VALERIA;PINESCHI, MAURO;CROTTI, PAOLO
2003-01-01
Abstract
[GRAPHICS] 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 beta-C-glycosides with excellent 1,4-regioselectivity and complete stereoselectivity for the beta-glycoside. Other organometallic reagents demonstrate more complex behavior in their reactions with epoxide 4.File in questo prodotto:
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