Showing papers on "Ferrier rearrangement published in 2000"
TL;DR: In this article, tri-O-acetyl-d-glucal 1 with various alcohols and phenols in the presence of InCl3/CH2Cl2 at ambient temperature gave the corresponding alkyl and aryl 2,3-unsaturated glycopyranosides in excellent yields with short reaction times and good anomeric selectivity.
83 citations
TL;DR: Scandium(III) trifluoromethanesulfonate was found to catalyze efficiently the O-glycosidation of 3,4,6-tri-O-acetyl-d-glucal with various alcohols and phenols to afford the corresponding 2,3-unsaturated glycosides in excellent yields with good anomeric selectivity as discussed by the authors.
Abstract: Scandium(III) trifluoromethanesulfonate is found to catalyze efficiently the O-glycosidation of 3,4,6-tri-O-acetyl-d-glucal with various alcohols and phenols to afford the corresponding 2,3-unsaturated glycosides in excellent yields with good anomeric selectivity.
15 citations
TL;DR: In this article, a general strategy for catalytic tin radical mediated, radical cascade reactions is proposed in which three rings are constructed in a single step, and the initial step in the tricyclisation process has been examined using 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides bearing unsaturated substituents at the 1-O and/or 4-O positions.
Abstract: A general strategy for catalytic tin radical mediated, radical cascade reactions is proposed in which three rings are constructed in a single step. The initial step in the tricyclisation process has been examined using 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides bearing unsaturated substituents at the 1-O and/or 4-O-positions. Substrates for cyclisation of substituents at the 1-O-position were prepared by a novel zinc chloride catalysed Ferrier rearrangement of tri-O-acetyl-D-glucal with unsaturated alcohols, whereas substrates for cyclisation of substituents at the 4-O-position were prepared by alkylation or acylation of ethyl 6-O-protected 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides. Propargyl substituents cyclise efficiently, but propenyl substituents less so. Propioloyl substituents undergo hydrostannylation without cyclisation.
10 citations
TL;DR: In this article, the treatment of tri-O acetyl-D-galactal with diverse alcohols in the presence of LiBF4 in CH3CN, furnished alkyl 2,3-unsaturated glycopyranosides 3-18 (50-86%).
Abstract: Treatment of tri-O acetyl-D-galactal 1 and tri-O-acetyl-D-glucal 2 with diverse alcohols in the presence of LiBF4 in CH3CN, furnished alkyl 2,3-unsaturated glycopyranosides 3-18 (50-86%).