A catalytic Koenigs-Knorr glycosylation based on acceptor activation with In(NTf2)3

Changwei Li, Haijing Liang, Zhan xin Zhang, Zhaoyan Wang, Lan Yu, Huanxiang Liu, Fengli An, Shaohua Wang, Lixia Ma, Weihua Xue

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

The development of efficient glycosylation methods is important for gaining better insight into biological processes of significance to medicinal chemistry. Herein, we describe an In(NTf2)3 -catalyzed Koenigs-Knorr glycosylation based on the activation of an alcoholic hydroxyl group. A catalytic amount of In(NTf2)3 enables effective glycosylation of diverse alcohols with peracylated aldosyl bromides as donors, leading to the stereoselective formation of a series of glycosides in satisfactory yields. The protocol is characterized by mild reaction conditions and good functional-group tolerance, while obviating any need for any additive. Moreover, the potential utility of this transformation is demonstrated by the convenient syntheses of key building blocks for biomolecules of medicinal relevance.

Original languageEnglish
Pages (from-to)3963-3970
Number of pages8
JournalTetrahedron
Volume74
Issue number29
DOIs
Publication statusPublished - 19 Jul 2018
Externally publishedYes

Keywords

  • Acceptor activation
  • Catalytic
  • In(NTf)
  • Koenigs-Knorr glycosylation
  • Stereoselective

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