Brønsted acid-catalyzed stereoselective allylation of exo-glycals with allyltrimethylsilane

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.

Name thesis:degree_name

Master of Science (MSc)

Discipline thesis:degree_discipline

Applied Bioscience

Grantor

University of Ontario Institute of Technology

Year dc:date.issued

2022

Author dc:creator

• Patel, Omik

Advisor dc:contributor.advisor

• Bolshan, Yuri

• exo-Glycals
• C,C-glycosides
• Allylation
• Brønsted acid
• Catalysis

Language dc:language.iso

en

Handle dc:identifier.uri

https://hdl.handle.net/10155/1519

OAI identifier oai:identifier

oai:ontariotechu.scholaris.ca:10155/1519