ol9b01231_si_001.pdf (16.32 MB)
Download file

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

Download (16.32 MB)
journal contribution
posted on 06.05.2019, 15:35 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.

History