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Catalytic Activation of Cis-Vicinal Diols by Boronic Acids: Site‑Selective Acylation of Carbohydrates

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journal contribution
posted on 06.05.2019, 15:35 authored by Naoyuki Shimada, Yuki Nakamura, Takayuki Ochiai, Kazuishi Makino
Site-selective acylation of unprotected carbohydrates by using stable, storable, and easily handled imidazole-containing organoboronic acid catalysts is described. This catalytic process with low catalyst loading enables the introduction of a wide variety of acyl functional groups into the equatorial position of cis-vicinal diols in unprotected hexapyranosides with excellent site selectivity. This is the first example that uses a Lewis base-containing boronic acid to enhance the nucleophilicity of hydroxy groups.