Kinetically Controlled α-Selective O-Glycosylation of Phenol Derivatives Using 2-Nitroglycals by a Bifunctional Chiral Thiourea Catalyst

Keisuke Yoshida, Yohei Kanoko, Kenichi Takao

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The highly α-selective organocatalytic glycosylation of phenol derivatives using 2-nitroglycals has been developed. The stereoselectivity of this reaction was kinetically controlled by a bifunctional thiourea catalyst, the chirality of which was crucial for obtaining the high α-selectivity. A variety of phenol derivatives were added to 2-nitrogalactal with excellent stereoselectivity. The reaction of 2-nitroglucal also achieved highly stereoselective glycosylation. The reaction was applied to the synthesis of glycopeptides.

Original languageEnglish
Pages (from-to)1230-1236
Number of pages7
JournalAsian Journal of Organic Chemistry
Volume5
Issue number10
DOIs
Publication statusPublished - 2016 Oct 1

Keywords

  • Michael addition
  • carbohydrates
  • glycosylation
  • organocatalysis

ASJC Scopus subject areas

  • Organic Chemistry

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