Perfluorophenylboronic acid-catalyzed direct α-stereoselective synthesis of 2-deoxygalactosides from deactivated peracetylated D-galactal.
- Resource Type
- Article
- Authors
- Tatina, Madhu Babu; Moussa, Ziad; Xia, Mengxin; Judeh, Zaher M. A.
- Source
- Chemical Communications. 10/18/2019, Vol. 55 Issue 81, p12204-12207. 4p.
- Subject
- *FUNCTIONAL groups
*NUCLEOPHILES
*DISACCHARIDES
*GROUP formation
- Language
- ISSN
- 1359-7345
Perfluorophenylboronic acid 1c catalyzes the direct stereoselective addition of alcohol nucleophiles to deactivated peracetylated D -galactal to give 2-deoxygalactosides in 55–88% yield with complete α-selectivity. The unprecedented results reported here also enable the synthesis of disaccharides containing the 2-deoxygalactose moiety directly from the deactivated peracetylated D -galactal. This convenient and metal-free glycosylation method works well with a wide range of alcohol nucleophiles as acceptors and tolerates a range of functional groups without the formation of the Ferrier byproduct and without the need for a large excess of nucleophiles or additives. The method is potentially useful for the synthesis of a variety of α-2-deoxygalactosides. [ABSTRACT FROM AUTHOR]