Reactions of 3-O-acetyl-2-C-ρ-tolylsulfonyl-D-arabino- and -D-ribo-hex-1-enitol derivatives with nucleophiles; the SN2′ mechanism is proved firstly in glycal derivatives

Article abstract of DOI:10.1016/S0040-4039(00)97461-6

Reactions of the title compounds with sodium methoxide and sodium borodeuteride were found to proceed mainly via the S_N2′ mechanism; nucleophiles selectively attacked the anomeric carbon atom from the same side of the leaving acetoxyl group at C-3.