Abstract
[reaction: see text] N-Mesyl aziridine 7alpha, a new activated vinyl aziridine derived from d-glucal, has been synthesized by cyclization of trans-N,O-dimesylate 6 with t-BuOK in anhydrous benzene. The reaction of 7alpha with alcohols, phenol, and monosaccharides (O-nucleophiles) leads to the corresponding 4-N-(mesylamino)-2,3-unsaturated-O-glycosides and disaccharides through a completely regioselective 1,4-addition process that proceeds with high or complete alpha-stereoselectivity.
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