Brønsted acid-catalyzed stereoselective allylation of exo-glycals with allyltrimethylsilane
dc.contributor.advisor | Bolshan, Yuri | |
dc.contributor.author | Patel, Omik | |
dc.date.accessioned | 2022-09-06T19:06:23Z | |
dc.date.available | 2022-09-06T19:06:23Z | |
dc.date.issued | 2022-08-01 | |
dc.identifier.uri | https://hdl.handle.net/10155/1519 | |
dc.description.abstract | Quaternary stereocenter on carbohydrate scaffolds is an important motif due to its presence in natural products and biologically active compounds. However, the preparation of C,C-glycosides is a challenge, and to date, many studies have failed to exploit exo-glycals as starting materials. The allylation methodologies of sugar lactol and sugar lactone starting materials suffer from poor regio- and stereoselectivity. Recently, we have developed a synthetic method for the allylation of exo-glycals using allyltrimethylsilane. This Brønsted acid-catalyzed transformation for the preparation of C,C-glycosides occurs readily in the presence of a tetrafluoroboric acid diethyl ether complex. In contrast to previously reported procedures, this reaction proceeds in a diastereoselective manner to afford α-allyl substituted pyranose. | en |
dc.description.sponsorship | University of Ontario Institute of Technology | en |
dc.language.iso | en | en |
dc.subject | exo-Glycals | en |
dc.subject | C,C-glycosides | en |
dc.subject | Allylation | en |
dc.subject | Brønsted acid | en |
dc.subject | Catalysis | en |
dc.title | Brønsted acid-catalyzed stereoselective allylation of exo-glycals with allyltrimethylsilane | en |
dc.type | Thesis | en |
dc.degree.level | Master of Science (MSc) | en |
dc.degree.discipline | Applied Bioscience | en |
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