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  • Title: Enantioselective conversion of primary alcohols to α-exo-methylene γ-butyrolactones via iridium-catalyzed C-C bond-forming transfer hydrogenation: 2-(alkoxycarbonyl)allylation.
    Author: Montgomery TP, Hassan A, Park BY, Krische MJ.
    Journal: J Am Chem Soc; 2012 Jul 11; 134(27):11100-3. PubMed ID: 22734694.
    Abstract:
    Upon exposure of acrylic ester 1 to alcohols 2a-i in the presence of a cyclometalated iridium catalyst modified by (-)-TMBTP, catalytic C-C coupling occurs, providing enantiomerically enriched 5-substituted α-exo-methylene γ-butyrolactones 3a-i. Bromination of the methylene butyrolactone products followed by zinc-mediated reductive aldehyde addition provides the disubstituted α-exo-methylene γ-butyrolactones 6a and 6b with good to excellent levels of diastereoselectivity.
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