ORGN 21 |
Sulfoxide covalent catalysis: Application to glycosidic bond formation
| Timothy A. Boebel, Department of Chemistry, University of Illinois at Urbana Champaign, 600 S Mathews Ave, Roger Adams Box 69-5, Urbana, IL 61801 and David Y. Gin, Department of Chemistry, University of Illinois at Urbana-Champaign, 600 S. Mathews Ave, Urbana, IL 61801. |
| The process of sulfoxide covalent catalysis is established in the context of a versatile dehydrative glycosylation reaction. Hemiacetal donors (1) are activated by benzenesulfonic anhydride and a dialkyl sulfoxide catalyst, n-Bu2SO, for the direct glycosylation of various nucleophiles (Nu-H). The sulfoxide catalyst functions uniquely in three capacities: first as an O-nucleophile, then as a S+-electrophile, and finally as a leaving group to accomplish turnover.  |
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