Chemistry Department Seminar Clay Bennett Tufts University. "Reagnet Controlled Approached to Stereoselective Glycosylation Reactions."
- 2/28/2014 | 3:00 PM – 4:00 PM
- Location: Druckenmiller Hall, Room 020
- Event Type: Seminar
- Sponsor: Chemistry
- Contact: Penny Westfall
- - Open to the Bowdoin Community -
Chemical glycosylation reactions typically rely on the intrinsic stereochemical information in the coupling partners to control selectivity (substrate control). A consequence of this is that extensive modification of the coupling partners, or optimization of reaction conditions, is often necessary to obtain stereoselective reactions, especially with so-called difficult linkages. To address this we have developed glycosylation reactions where the promoter exerts absolute control over the stereochemical outcome of the reaction (reagent control). Using this approach in the 2-deoxy series we have found that it is possible to obtain either anomer of a particular glycosidic linkage from the same coupling partners simply by changing the promoter. The scope of this approach with different classes of donors, and mechanistic considerations will also be discussed.