Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts.

  title={Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts.},
  author={Alexander Seitz and Raffael C. Wende and Emily K Roesner and Dominik Niedek and Christopher Topp and Avene C. Colgan and Eoghan M McGarrigle and Peter Richard Schreiner},
  journal={The Journal of organic chemistry},
Herein, we report the oligopeptide-catalyzed site-selective acylation of partially protected monosaccharides. We identified catalysts that invert site-selectivity compared to N-methylimidazole, which was used to determine the intrinsic reactivity, for 4,6-O-protected glucopyranosides (trans-diols) as well as 4,6-O-protected mannopyranosides (cis-diols). The reaction yields up to 81% of the inherently unfavored 2-O-acetylated products with selectivities up to 15:1 using mild reaction conditions… 
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