Expanding cyclitol structural diversity by biocatalysis and metalocatalysis. A click chemistry approach

Abstract

The palladium catalyzed cross-coupling reaction of phenyltrifluoroborate with a chemoenzymatically derived bromoazidoconduritol, combined with 1,3-dipolar cycloaddition, with a variety of alkynes is described. Fourteen new compounds were synthesized in moderate to good yields. The click chemistry reaction can be effected by using sodium ascorbate and CuSO4· 5H2O as catalyst in toluene-H2O at room temperature. © 2010 Springer Science+Business Media B.V.