Asymmetric epoxidation of cis-alkenes with arabinose-derived ketones: enantioselective synthesis of the side chain of Taxol®

Tony Kung Ming Shing, To Luk, Chi M. Lee

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The ee values of asymmetric epoxidation of cis-ethyl cinnamate 15 with arabinose-derived ketones as catalyst and Oxone® as the terminal oxidant were found to increase inversely with the size of the catalyst acetal blocking group. Ketone catalyst 2, with the least bulky methoxy acetal group, displayed the best enantioselectivity and afforded ethyl (2R,3R)-3-phenylglycidate 16 in 68% ee. Epoxide 16 was readily converted into a protected side chain of Taxol® in five steps with an overall yield of 89%. The enantioselectivity of the epoxidation of other cis-alkenes was moderate to poor.

Original languageEnglish
Pages (from-to)6621-6629
Number of pages9
JournalTetrahedron
Volume62
Issue number28
DOIs
Publication statusPublished - 2006 Jul 10
Externally publishedYes

Fingerprint

Acetals
Arabinose
Epoxidation
Alkenes
Paclitaxel
Ketones
Enantioselectivity
Catalysts
Epoxy Compounds
Oxidants
potassium peroxymonosulfuric acid
ethyl cinnamate

Keywords

  • Asymmetric synthesis
  • Dioxirane
  • Epoxidation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Asymmetric epoxidation of cis-alkenes with arabinose-derived ketones : enantioselective synthesis of the side chain of Taxol®. / Shing, Tony Kung Ming; Luk, To; Lee, Chi M.

In: Tetrahedron, Vol. 62, No. 28, 10.07.2006, p. 6621-6629.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Luk, To ; Lee, Chi M. / Asymmetric epoxidation of cis-alkenes with arabinose-derived ketones : enantioselective synthesis of the side chain of Taxol®. In: Tetrahedron. 2006 ; Vol. 62, No. 28. pp. 6621-6629.
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