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

Farwick, Andreas and Engelhart, Jens and Tverskoy, Olena and Welter, Carolin and Umlauf, Quendolin and Rominger, Frank and Kerr, William and Helmchen, Gunter (2011) Bicyclic cyclopentenones via the combination of an iridium- catalyzed allylic substitution with a diastereoselective intramolecular Pauson–Khand reaction. Advanced Synthesis and Catalysis, 353 (2-3). pp. 349-370. ISSN 1615-4150

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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.