Jump to Main Content
Enantioselective Conversion of Primary Alcohols to α-exo-Methylene γ-Butyrolactones via Iridium-Catalyzed C–C Bond-Forming Transfer Hydrogenation: 2-(Alkoxycarbonyl)allylation
- Montgomery, T. Patrick, Hassan, Abbas, Park, Boyoung Y., Krische, Michael J.
- Journal of the American Chemical Society 2012 v.134 no.27 pp. 11100-11103
- alcohols, aldehydes, bromination, catalysts, chemical bonding, enantiomers, hydrogenation, iridium
- 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.