Synthesis of enantiomerically pure cyclohex-2-en-1-ols: Development of novel multicomponent reactions

Dirk Strübing, Anett Kirschner, Helfried Neumann, Sandra Hübner, Stefan Klaus, Uwe T. Bornscheuer, Matthias Beller

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

Multicomponent reactions of aldehydes, dienophiles, and alcohols or carboxylic acid anhydrides have been developed for the first time. In situ generation of 1-acyloxy- and 1-alkoxy-1,3-butadiene derivatives in toluene in the presence of electron-deficient dienophiles provides selective and efficient access to functionalized cyclohex-2-ene-1-ols in good yields. Subsequent enzyme-catalyzed kinetic resolution gave the corresponding enantiomers with high enantioselectivity.

Original languageEnglish
Pages (from-to)4210-4218
Number of pages9
JournalChemistry - A European Journal
Volume11
Issue number14
DOIs
StatePublished - 4 Jul 2005
Externally publishedYes

Keywords

  • Cyclohexenes
  • Enzymes
  • Kinetic resolution
  • Multicomponent reactions

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