{"id":{"repo_id":"uoit","oai_identifier":"oai:ontariotechu.scholaris.ca:10155/1519"},"canonical_url":"https://search.dev.ndltd.org/etd/uoit/oai:ontariotechu.scholaris.ca:10155/1519","repository":{"repo_id":"uoit","name":"Ontario Institute of Technology","base_url":"https://ontariotechu.scholaris.ca/server/oai/request"},"display":{"title":"Brønsted acid-catalyzed stereoselective allylation of exo-glycals with allyltrimethylsilane","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.","abstract_html":"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.","abstract_has_math":false,"creators":["Patel, Omik"],"institution":"University of Ontario Institute of Technology","degree_name":"Master of Science (MSc)","degree_level":null,"degree_discipline":"Applied Bioscience","degree_department":null,"school":null,"contributors":[],"advisors":["Bolshan, Yuri"],"committee_chairs":[],"committee_members":[],"year":2022,"date_issued":"2022-08-01","date_published":"2022-08-01","updated_at":"2026-07-24T05:35:18Z","subjects":["exo-Glycals","C,C-glycosides","Allylation","Brønsted acid","Catalysis"],"languages":["en"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://hdl.handle.net/10155/1519","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Bolshan, Yuri"]},{"key":"dc:creator","label":"Author","values":["Patel, Omik"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2022-09-06T19:06:23Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2022-09-06T19:06:23Z"]},{"key":"dc:date.issued","label":"Date","values":["2022-08-01"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Applied Bioscience"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (MSc)"]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Ontario Institute of Technology"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["exo-Glycals","C,C-glycosides","Allylation","Brønsted acid","Catalysis"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["en"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://hdl.handle.net/10155/1519"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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."]},{"key":"dc:title","label":"Title","values":["Brønsted acid-catalyzed stereoselective allylation of exo-glycals with allyltrimethylsilane"]}]}],"canonical_facts":{"dc:contributor.advisor":["Bolshan, Yuri"],"dc:creator":["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: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."],"dc:identifier.uri":["https://hdl.handle.net/10155/1519"],"dc:language.iso":["en"],"dc:subject":["exo-Glycals","C,C-glycosides","Allylation","Brønsted acid","Catalysis"],"dc:title":["Brønsted acid-catalyzed stereoselective allylation of exo-glycals with allyltrimethylsilane"],"dc:type":["Thesis"],"thesis:degree_discipline":["Applied Bioscience"],"thesis:degree_name":["Master of Science (MSc)"],"thesis:institution_name":["University of Ontario Institute of Technology"]},"updated_at":"2026-07-24T05:35:18Z"}