AMINO ALCOHOL AND AMINO SUGAR SYNTHESIS BY BENZOYLCARBAMATE CYCLIZATION

The sodium anion (3) of an alcohol-derived benzoylcarbamate (2) may be used to deliver an amino nitrogen intramolecularly to electrophilic carbon centers such as bromides, epoxides, and triflates, giving rise to amino alcohol and amino diol derivatives of general form 4–6. A procedure for selective monotriflation of carbohydrate diols is described that exploits the enhanced reactivity of carbohydrate hydroxyls flanked by a cis, vicinal ether oxygen. Subsequent benzoylcarbamate formation and cyclization allows the conversion of several sugars to amino sugars (47, 54, 74, 80). However, the cyclization occurs on the carbonyl oxygen if the triflate site is hindered (63 and 67). © 1990, American Chemical Society. All rights reserved.