Arabinose-derived ketones as catalysts for asymmetric epoxidation of alkenes

Tony K.M. Shing, Gulice Y.C. Leung, To Luk

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Readily available arabinose-derived ketones, containing a tunable butane-2,3-diacetal as the steric blocker, displayed increasing enantioselectivity (up to 90% ee) with the size of the acetal alkyl group in catalytic asymmetric epoxidation of trans-disubstituted and trisubstituted alkenes. The stereochemical communication between our ketone catalysts and the alkene substrates is mainly due to steric effect, and electronic effect involving π-π interaction between phenyl groups of substrate and of catalyst did not appear to be operative in our system.

Original languageEnglish
Pages (from-to)7279-7289
Number of pages11
JournalJournal of Organic Chemistry
Volume70
Issue number18
DOIs
Publication statusPublished - 2005 Sep 2

ASJC Scopus subject areas

  • Organic Chemistry

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