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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, T. Patrick, Hassan, Abbas, Park, Boyoung Y., Krische, Michael J.
Source:
Journal of the American Chemical Society 2012 v.134 no.27 pp. 11100-11103
ISSN:
1520-5126
Subject:
alcohols, aldehydes, bromination, catalysts, chemical bonding, enantiomers, hydrogenation, iridium
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.
Agid:
5385900