Enantioselective conversion of primary alcohols to α-exo-methylene γ-butyrolactones via iridium-catalyzed C-C bond-forming transfer hydrogenation: 2-(alkoxycarbonyl)allylation.
作者： T. Patrick Montgomery , Abbas Hassan , Boyoung Y. Park , Michael J. Krische
DOI: 10.1021/JA303839H
关键词: Chemistry 、 Catalysis 、 Aldehyde 、 Organic chemistry 、 Halogenation 、 Medicinal chemistry 、 Iridium 、 Allyl compound 、 Methylene 、 Transfer hydrogenation 、 Enantioselective synthesis
摘要: Upon exposure of acrylic ester 1 to alcohols 2a-i in the presence 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 methylene butyrolactone products followed zinc-mediated reductive aldehyde addition provides disubstituted 6a and 6b with good excellent levels diastereoselectivity.
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