Enantioselective synthesis of phospholenes via asymmetric organocatalytic alkene isomerization

Lukas Hintermann, Marco Schmitz

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

An asymmetric synthesis of the 2,5-diphenylphosphol-2-ene fragment (≥95% ee) has been realized via enantioselective Cinchona-alkaloid catalyzed double bond isomerization of a meso-2,5-diphenylphosphol-3-ene amide to a 2,5-diphenylphosphol-2-ene amide (up to 83% ee), followed by enantiomeric enrichment to ≥95% ee by crystallization. The 2,5-diphenylphosphol-2-ene amide (a cyclic phosphinic acid amide) was hydrolyzed to the 2,5-diphenylphosphol-2-ene acid (a cyclic phosphinic acid) with retention of configuration at C-5.

Original languageEnglish
Pages (from-to)1469-1473
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume350
Issue number10
DOIs
StatePublished - 7 Jul 2008
Externally publishedYes

Keywords

  • Alkaloids
  • Alkenes
  • Asymmetric catalysis
  • Cinchona alkaloids
  • Isomerization
  • Phosphorus heterocycles

Fingerprint

Dive into the research topics of 'Enantioselective synthesis of phospholenes via asymmetric organocatalytic alkene isomerization'. Together they form a unique fingerprint.

Cite this