Synthesis of pyranoid and furanoid glycals from glycosyl sulfoxides by treatment with organolithium reagents

AM Gomez, M Casillas, A Barrio…

Index: Gomez, Ana M.; Casillas, Marta; Barrio, Aitor; Gawel, Anna; Lopez, J. Cristobal European Journal of Organic Chemistry, 2008 , # 23 p. 3933 - 3942

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Citation Number: 9

Abstract

Abstract Glycosyl sulfoxides can be conveniently transformed into pyranoid or furanoid glycals by treatment with organolithium reagents. The more likely reaction pathway involves a sulfoxide/metal exchange reaction to generate a glycosyllithium derivative that undergoes β-elimination of its C-2 substituent.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

~62%

~87%

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