Catalytic asymmetric epoxidation of alkenes with arabinose-derived ketones containing a cyclohexane-1,2-diacetal

Tony Kung Ming Shing, To Luk

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The effect of diol blocking groups, cyclohexane-1,2-diacetal verses butane-1,2-diacetal, on the asymmetric epoxidation of trans- and cis-alkenes by arabinose-derived ketones is reported. The ketone catalysts with a cyclohexane-1,2-acetal display similar asymmetric induction as those catalysts with a butane-1,2-diacetal in most cases. For (E)-1-benzyloxy-4-hexene, the ee of the enantioselective epoxidation has reached 61% with the cyclohexane-1,2-dineopentyl acetal ketone catalyst.

Original languageEnglish
Pages (from-to)883-886
Number of pages4
JournalTetrahedron Asymmetry
Volume20
Issue number6-8
DOIs
Publication statusPublished - 2009 May 7
Externally publishedYes

Fingerprint

Arabinose
epoxidation
Epoxidation
Alkenes
Cyclohexane
Ketones
ketones
cyclohexane
alkenes
Olefins
acetals
Acetals
Butane
butanes
catalysts
Catalysts
hexenes
induction
butane

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Catalytic asymmetric epoxidation of alkenes with arabinose-derived ketones containing a cyclohexane-1,2-diacetal. / Shing, Tony Kung Ming; Luk, To.

In: Tetrahedron Asymmetry, Vol. 20, No. 6-8, 07.05.2009, p. 883-886.

Research output: Contribution to journalArticle

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