Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides

Carlos Palo Nieto, Abhijit Sau, Ryan Williams, Carmen Galan

Research output: Contribution to journalArticle (Academic Journal)peer-review

44 Citations (Scopus)
302 Downloads (Pure)

Abstract

A practical approach for the ∝-stereoselective synthesis of deoxyglycosides using cooperative Brønsted acid-type organocataly-sis has been developed. The method is tolerant of a wide range of glycoside donors and acceptors and its versatility is exempli-fied in the one-pot synthesis of a trisaccharide. Mechanistic studies suggest that thiourea-induced acid amplification of the chi-ral acid via H-bonding is key for the enhancement in reaction rate and yield, while stereocontrol is dependent on the chirality of the acid.
Original languageEnglish
Pages (from-to)407–414
Number of pages8
JournalJournal of Organic Chemistry
Volume82
Issue number1
Early online date22 Dec 2016
DOIs
Publication statusPublished - 6 Jan 2017

Keywords

  • Cooperative catalysis
  • organocatalysis
  • chiral phosphoric acids
  • chiral acetals
  • stereoselectivity
  • deoxyglycosides

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