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  • Title: Asymmetric intermolecular Pauson-Khand reactions of unstrained olefins: the (o-dimethylamino)phenylsulfinyl group as an efficient chiral auxiliary.
    Author: Rodríguez Rivero M, De La Rosa JC, Carretero JC.
    Journal: J Am Chem Soc; 2003 Dec 10; 125(49):14992-3. PubMed ID: 14653726.
    Abstract:
    The first asymmetric version of intermolecular Pauson-Khand reactions of unstrained alkenes is described. Generally simple acyclic alkenes exhibit low reactivity and regioselectivity in intermolecular Pauson-Khand reactions; however, o-(dimethylamino)phenyl vinyl sulfoxide reacts under very mild conditions with a wide variety of terminal alkynes in a completely regioselective and highly stereoselective manner. The utility of the resulting 5-sulfinyl-2-cyclopentenones in asymmetric synthesis is illustrated by a very short enantioselective synthesis of the antibiotic (-)-pentenomycin I.
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