Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides

• Main Authors: Tatina, Madhu Babu, Xia, Mengxin, Rao, Peilin, Judeh, Zaher M. A.
• Other Authors: School of Chemical and Biomedical Engineering
• Format: Article
• Language: English
• Published: 2020
• Subjects: Engineering::Chemical engineering; C-, O-, N- And S-linked Glycosides; Enosides
• Online Access: https://hdl.handle.net/10356/137429
• Institution: Nanyang Technological University

A convenient protocol was developed for the synthesis of 2,3-unsaturated C-, O-, N- and S-linked glycosides (enosides) using 20 mol % perflurophenylboronic acid catalyst via Ferrier rearrangement. Using this protocol, D-glucals and L-rhamnals reacted with various C-, O-, N- and S-nucleophiles to giv...