Recognition and Site‐Selective Transformation of Monosaccharides by Using Copper(II) Catalysis |
| |
| Authors: | Dr I‐Hon Chen Kevin G M Kou Diane N Le Colin M Rathbun Prof?Dr Vy M Dong |
| |
| Institution: | 1. Department of Chemistry, University of California, Irvine, Natural Sciences 1, University of California, Irvine, California 92697 (USA);2. Department of Chemistry, University of Toronto, 80 St. George Street (Canada) |
| |
| Abstract: | We demonstrate copper(II)‐catalyzed acylation and tosylation of monosaccharides. Various carbohydrate derivatives, including glucopyranosides and ribofuranosides, are obtained in high yields and regioselectivities. Using this versatile strategy, the site of acylation can be switched by choice of ligand. Preliminary mechanistic studies support nucleophilic addition of a copper–sugar complex to the acyl chloride to be turnover limiting. |
| |
| Keywords: | carbohydrates catalysis molecular recognition site‐selective functionalization transition metals |
|
|
