Bicyclic cyclopentenones via the combination of an iridium- catalyzed allylic substitution with a diastereoselective intramolecular Pauson–Khand reaction

Andreas Farwick, Jens Engelhart, Olena Tverskoy, Carolin Welter, Quendolin Umlauf, Frank Rominger, William Kerr, Gunter Helmchen

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Enantioselective syntheses of bicyclic cyclopentenones are described. Key steps are an Ir-catalyzed allylic substitution and an intramolecular diastereoselective Pauson-Khand reaction. The diastereoselectivity of the Pauson-Khand reaction was found to be crucially dependent on the unit connecting the propargylic and the olefinic units of the precursor. Very high degrees of diastereoselection were obtained with an NBoc unit as connector. This methodology has been illustrated by application within an enantioselective formal total synthesis of (-)-α-kainic acid.
LanguageEnglish
Pages349-370
Number of pages22
JournalAdvanced Synthesis and Catalysis
Volume353
Issue number2-3
DOIs
Publication statusPublished - 11 Feb 2011

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Iridium
Substitution reactions
Kainic Acid
Acids
cyclopentenone

Keywords

  • alkyne ligands
  • enantioselective total synthesis
  • asymmetric total synthesis
  • Pauson-Khand reaction
  • alkaloids
  • (-)
  • Japanese hop ether
  • iridium
  • allylic substitution
  • efficient chiral auxiliary
  • amine N-oxide
  • formal total-synthesis
  • asymmetric catalysis

Cite this

Farwick, Andreas ; Engelhart, Jens ; Tverskoy, Olena ; Welter, Carolin ; Umlauf, Quendolin ; Rominger, Frank ; Kerr, William ; Helmchen, Gunter. / Bicyclic cyclopentenones via the combination of an iridium- catalyzed allylic substitution with a diastereoselective intramolecular Pauson–Khand reaction. In: Advanced Synthesis and Catalysis. 2011 ; Vol. 353, No. 2-3. pp. 349-370.
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abstract = "Enantioselective syntheses of bicyclic cyclopentenones are described. Key steps are an Ir-catalyzed allylic substitution and an intramolecular diastereoselective Pauson-Khand reaction. The diastereoselectivity of the Pauson-Khand reaction was found to be crucially dependent on the unit connecting the propargylic and the olefinic units of the precursor. Very high degrees of diastereoselection were obtained with an NBoc unit as connector. This methodology has been illustrated by application within an enantioselective formal total synthesis of (-)-α-kainic acid.",
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Bicyclic cyclopentenones via the combination of an iridium- catalyzed allylic substitution with a diastereoselective intramolecular Pauson–Khand reaction. / Farwick, Andreas; Engelhart, Jens; Tverskoy, Olena; Welter, Carolin; Umlauf, Quendolin; Rominger, Frank; Kerr, William; Helmchen, Gunter.

In: Advanced Synthesis and Catalysis, Vol. 353, No. 2-3, 11.02.2011, p. 349-370.

Research output: Contribution to journalArticle

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AU - Tverskoy, Olena

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AU - Rominger, Frank

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