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DOI: 10.1055/s-0033-1340411
Phosphoric Acid Mediated Glycosylation and Alcohol-Chirality Recognition
Publication History
Publication Date:
13 December 2013 (online)
![](https://www.thieme-connect.de/media/synfacts/201401/i_b124_s1_10-1055_s-0033-1340411.gif)
Significance
Toshima and co-workers report a highly β-selective glycosylation of α-trichloroacetimidates 1α with various secondary alcohols. The diastereoselectivity is moderate to excellent, and the reaction is mediated by the phosphoric acid (S)-3. According to mechanistic studies, the exclusive β-selectivities are obtained through a (S)-3-mediated SN2 reaction pathway. The methodology was also applied to the total synthesis of a natural flavan glycoside using a racemic aglycone.
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Comment
Glycosylation is an important synthetic method to construct sugar moiety containing compounds. Here, the authors report a novel Brønsted acid mediated glycosylation, and a kinetic resolution of secondary alcohols occurs during the process at the same time. This methodology provides a straightforward way for the synthesis of sugar-derived products with high stereoselectivity.
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![](https://www.thieme-connect.de/media/synfacts/201401/i_b124_s1_10-1055_s-0033-1340411.gif)