Chiral Brønsted acid mediated glycosylation with recognition of alcohol chirality

Tomoya Kimura, Maiko Sekine, Daisuke Takahashi, Kazunobu Toshima

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

Sugar sugar: In the glycosylation of racemic alcohols with 1 using the chiral phosphoric acid 2 as an activator, one enantiomer of the racemic alcohol selectively reacts with 1 to give the corresponding glycoside with good to excellent α/β-stereo- and diastereoselectivity in high yield. The reaction was successfully applied to the synthesis of a chiral natural flavan glycoside using a racemic aglycon.

Original languageEnglish
Pages (from-to)12131-12134
Number of pages4
JournalAngewandte Chemie - International Edition
Volume52
Issue number46
DOIs
Publication statusPublished - 2013 Nov 11

Fingerprint

Glycosylation
Glycosides
Chirality
Sugars
Alcohols
Acids
Enantiomers
Phosphoric acid
phosphoric acid

Keywords

  • diastereoselectivity
  • glycosides
  • glycosylation
  • organocatalysis
  • synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Medicine(all)

Cite this

Chiral Brønsted acid mediated glycosylation with recognition of alcohol chirality. / Kimura, Tomoya; Sekine, Maiko; Takahashi, Daisuke; Toshima, Kazunobu.

In: Angewandte Chemie - International Edition, Vol. 52, No. 46, 11.11.2013, p. 12131-12134.

Research output: Contribution to journalArticle

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