Catalytic asymmetric epoxidation of alkenes with arabinose-derived uloses

Tony Kung Ming Shing, Yiu C. Leung, Kwan W. Yeung

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Four L-erythro-2-uloses were readily prepared from L-arabinose via a reaction sequence involving Fischer glycosidation, acetalization and oxidation. Bulky steric sensors at the anomeric center could enhance the stereoselectivity of the dioxirane epoxidation and one of the uloses performed with good enantioselectivity towards trans-stilbene (up to 90% ee). However, the catalysts decomposed during the epoxidation and the maximum chemical yield was only 13% under the basic conditions. Three L-threo-3-uloses could overcome the decomposition problem based on the electron withdrawing effect of the ester group(s) α to the ketone functionality. The best chemical yield was up to 93% using a ketone with two flanking ester groups. One of the improved uloses displayed moderate enantioselectivity towards trans-disubstituted and trisubstituted alkenes (40-68% ee).

Original languageEnglish
Pages (from-to)2159-2168
Number of pages10
JournalTetrahedron
Volume59
Issue number12
DOIs
Publication statusPublished - 2003 Mar 17
Externally publishedYes

Fingerprint

Arabinose
Epoxidation
Enantioselectivity
Alkenes
Ketones
Esters
Stereoselectivity
Stilbenes
Electrons
Decomposition
Oxidation
Catalysts
Sensors
dioxirane

Keywords

  • Arabinose
  • Asymmetric epoxidation
  • Ulose

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Catalytic asymmetric epoxidation of alkenes with arabinose-derived uloses. / Shing, Tony Kung Ming; Leung, Yiu C.; Yeung, Kwan W.

In: Tetrahedron, Vol. 59, No. 12, 17.03.2003, p. 2159-2168.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Leung, Yiu C. ; Yeung, Kwan W. / Catalytic asymmetric epoxidation of alkenes with arabinose-derived uloses. In: Tetrahedron. 2003 ; Vol. 59, No. 12. pp. 2159-2168.
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