Asymmetric desymmetrization of the diallyl acetals of alkynals by the enantioselective Pauson-Khand-type reaction catalysts

Eun Kim Dong, Hyung Lee Bo, Mudigonda Rajagopalasarma, Jean Pierre Genêt, Virginie Ratovelomanana-Vidal, Nakcheol Jeong

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10 Citations (Scopus)

Abstract

Asymmetric desymmetrization of the di-allyl acetals of alkynal (1) by an enantioselective Pauson-Khand-type reaction catalyst was studied. The corresponding 5-oxabicyclo[3.3.0]octenones (2) were obtained as a mixture of diastereomers (2a and 2b), which were hydrolyzed to afford a single enantiomer (3), in high yields (up to 88%) as well as excellent enantioselectivities (up to 97%).

Original languageEnglish
Pages (from-to)2695-2700
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume350
Issue number17
DOIs
Publication statusPublished - 2008 Nov 17

Keywords

  • Asymmetrric desymmetrization
  • Atrop-isomeric ligands
  • Enantioselective
  • Pauson-Khand reaction
  • Rhodium(I)

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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    Dong, E. K., Bo, H. L., Rajagopalasarma, M., Genêt, J. P., Ratovelomanana-Vidal, V., & Jeong, N. (2008). Asymmetric desymmetrization of the diallyl acetals of alkynals by the enantioselective Pauson-Khand-type reaction catalysts. Advanced Synthesis and Catalysis, 350(17), 2695-2700. https://doi.org/10.1002/adsc.200800514