Chiral fluoro ketones for catalytic asymmetric epoxidation of alkenes with oxone

Scott E. Denmark, Hayao Matsuhashi

Research output: Contribution to journalArticle

Abstract

Two structurally dissimilar, chiral fluoro ketones have been prepared and their potential as enantioselective catalysts for asymmetric epoxidation with Oxone has been evaluated. The tropinone-based ketone (-)-5 was easily prepared and showed excellent reactivity but only modest enantioselectivity. The biphenyl-based ketone (-)-6 was prepared in a somewhat lengthy synthesis (along with its monofluoro and geminal fluoro analogues). This ketone exhibited only modest reactivity; 30 mol % of (-)-6 was needed to bring about complete conversion in a reasonable time. The enantioselectivity of this catalyst was generally much higher, but again very substrate dependent.

Original languageEnglish (US)
Pages (from-to)3479-3486
Number of pages8
JournalJournal of Organic Chemistry
Volume67
Issue number10
DOIs
StatePublished - May 17 2002

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ASJC Scopus subject areas

  • Organic Chemistry

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