Stereoselective Synthesis of Iminosugar 2-Deoxy(thio)glycosides from Bicyclic Iminoglycal Carbamates Promoted by Cerium(IV) Ammonium Nitrate and Cooperative Brønsted Acid-Type Organocatalysis

Irene Herrera-González, Elena M Sánchez-Fernández, Abhijit Sau, Cristina Nativi, José M García Fernández, M Carmen Galán*, Carmen Ortiz Mellet*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

Abstract

The first examples of iminosugar-type 2-deoxy(thio)glycoside mimetics are reported. The key step is the activation of a bicyclic iminoglycal carbamate to generate a highly reactive acyliminium cation. Cerium(IV) ammonium nitrate efficiently promoted the formation of 2-deoxy S-glycosides in the presence of thiols, probably by in situ generation of catalytic HNO3, with complete α-stereoselectivity. Cooperative phosphoric acid/Schreiner's thiourea organocatalysis proved better suited for generating 2-deoxy O-glycosides, significantly broadening the scope of the approach.

Original languageEnglish
Pages (from-to)5038-5047
Number of pages10
JournalJournal of Organic Chemistry
Volume85
Issue number7
Early online date11 Mar 2020
DOIs
Publication statusPublished - 3 Apr 2020

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