Asymmetric epoxidation catalyzed by D-glucose-derived uloses

Tony Kung Ming Shing, Gulice Y.C. Leung

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

Three ulose catalysts (1-3) were prepared from D-glucose via an intramolecular nitrile oxide cycloaddition (INOC) as the key step. The enantioselectivity of ulose 2 and 3 in asymmetric epoxidation was poor (up to 26% ee). Ulose 1 afforded good chemical yields (up to 83% yield) and the enantiomeric excess is up to 71% for the formation of (-)-trans-stilbene oxide.

Original languageEnglish
Pages (from-to)7545-7552
Number of pages8
JournalTetrahedron
Volume58
Issue number37
DOIs
Publication statusPublished - 2002 Sep 9
Externally publishedYes

Fingerprint

Nitriles
Epoxidation
Cycloaddition
Enantioselectivity
Cycloaddition Reaction
Oxides
Glucose
Catalysts
stilbene oxide

Keywords

  • Asymmetric epoxidation
  • D-glucose
  • Ulose

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Asymmetric epoxidation catalyzed by D-glucose-derived uloses. / Shing, Tony Kung Ming; Leung, Gulice Y.C.

In: Tetrahedron, Vol. 58, No. 37, 09.09.2002, p. 7545-7552.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Leung, Gulice Y.C. / Asymmetric epoxidation catalyzed by D-glucose-derived uloses. In: Tetrahedron. 2002 ; Vol. 58, No. 37. pp. 7545-7552.
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