Organic letters

Assembling heterocycle-tethered C-glycosyl and α-amino acid residues via 1, 3-dipolar cycloaddition reactions

A Dondoni, PP Giovannini, A Massi

Index: Dondoni, Alessandro; Giovannini, Pier Paolo; Massi, Alessandro Organic Letters, 2004 , vol. 6, # 17 p. 2929 - 2932

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Citation Number: 136

Abstract

The 1, 3-dipolar cycloadditions of C-glycosyl nitrile oxides and acetylenes to an alkyne and an azide, respectively, bearing a masked glycinyl moiety furnished disubstituted isoxazoles and triazoles. Unveiling the glycinyl group in these cycloadducts afforded C-glycosyl α- amino acids in which the two bioactive entities were tethered through rigid five-membered heterocycles. Optimized entries to the same compounds involved the use of unmasked but ...