Theses and Dissertations at Montana State University (MSU)
Permanent URI for this collectionhttps://scholarworks.montana.edu/handle/1/733
Browse
6 results
Search Results
Item Stereoselective transformations of oxygen-bearing ring compounds(Montana State University - Bozeman, College of Letters & Science, 1988) Bartelt, Karen ElizabethItem Pinacol rearrangement : chemistry of 4,7,8,9-tetrahydrophthalans, a synthesis of frontalin(Montana State University - Bozeman, College of Letters & Science, 1971) Otzenberger, Rodney DaleItem Stereoselective synthetic methodologies : mechanistic studies toward natural products(Montana State University - Bozeman, College of Letters & Science, 1987) Copp, Richard RonaldItem Studies on pinacol chemistry(Montana State University - Bozeman, College of Letters & Science, 1985) Bruss, Dan R.Item Determination of the relative steric sizes of alkyl groups using a calculational approach(Montana State University - Bozeman, College of Letters & Science, 1986) Bowler, Ann MarieItem Palladium (II)-catalyzed stereoselective formation of [alpha]-O-glycosides(Montana State University - Bozeman, College of Letters & Science, 2007) Schuff, Brandon Patrick; Chairperson, Graduate Committee: Hien NguyenThe development of new methods for stereoselective formation of a- or *-Oglycosides has been extensively investigated due to the critical roles carbohydrates play in a variety of biological systems. To date, many efforts have focused on developing new methods and reagents for the generation of isolated glycosyl donors which subsequently undergo glycosidic bond formation with nucleophilic glycosyl acceptors. Despite their potential applications to complex carbohydrate synthesis, each of these methods relies on the nature of the substrates to stereoselectively control the formation of glycosidic bonds. Recently, the use of glycal derivatives as glycosyl donors has been utilized in p- allylpalladium strategies for the stereoselective synthesis of O-glycosides. However, due to the poor reactivity of the glycal donors as well as the alcohol nucleophiles, these groups utilized the more activated pyranone donors. Lee, who recognized the challenge in this approach, utilized Zn(II) ion to activate both the alcohol acceptors for the nucleophilic addition and the glycal donors for the ionization.