Asymmetric synthesis of cyclic hydroxy ketones derived from enol ethers via sharpless asymmetric dihydroxylation. A study in the correlation of the enol ether chain length and enantioselectivity

Benjamin F. Marcune, Sandor Karady, Paul J. Reider, Ross A. Miller, Mirlinda Biba, Lisa DiMichele, Robert A. Reamer

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

The Sharpless asymmetric dihydroxylation reaction of enol ethers derived from their corresponding cyclic ketones, gave α-hydroxyketones with high enantioselectivity. The enantiomeric excess was found to be proportional to the length of the unbranched enol ether chain with a maximum ee for the pentyl enol ether. An efficient synthesis of α-hydroxy chromanone in >90% ee was demonstrated using this method.

Original languageEnglish (US)
Pages (from-to)8088-8091
Number of pages4
JournalJournal of Organic Chemistry
Volume68
Issue number21
DOIs
StatePublished - Oct 17 2003
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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