Retro-Michael type reactions applied to PSE acetals protecting monosaccharides led either to complete removal or to ring-cleavage. In protic medium, application of standard basic conditions resulted in acetal deprotection, while the use of butyl lithium in aprotic medium allowed controlled ring-cleavage. A regioand stereoselective C- over O-alkylation was observed during the process. Furthermore, depending on the substrates and the reaction conditions involved, new carbohydrate-derived b-alkoxyvinyl sulfones were obtained with varying regioselectivity.
Carbohydrate-derived PSE acetals: controlled base-induced ring cleavage
DE LUCCHI, Ottorino;
2012-01-01
Abstract
Retro-Michael type reactions applied to PSE acetals protecting monosaccharides led either to complete removal or to ring-cleavage. In protic medium, application of standard basic conditions resulted in acetal deprotection, while the use of butyl lithium in aprotic medium allowed controlled ring-cleavage. A regioand stereoselective C- over O-alkylation was observed during the process. Furthermore, depending on the substrates and the reaction conditions involved, new carbohydrate-derived b-alkoxyvinyl sulfones were obtained with varying regioselectivity.File in questo prodotto:
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Tetrahedron 2012, 68, 544.pdf
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