Enantioselective Nickel-Catalyzed anti-Arylmetallative Cyclizations onto Acyclic Ketones |
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| Authors: | Harley Green Dr. Stephen P. Argent Prof. Hon Wai Lam |
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| Affiliation: | 1. The GlaxoSmithKline Carbon Neutral Laboratories for, Sustainable Chemistry, University of Nottingham, Jubilee Campus, Triumph Road, Nottingham, NG7 2TU UK;2. School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD UK |
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| Abstract: | Domino reactions involving nickel-catalyzed additions of (hetero)arylboronic acids to alkynes, followed by cyclization of the alkenylnickel intermediates onto tethered acyclic ketones to give chiral tertiary-alcohol-containing products in high enantioselectivities, are described. The reversible E/Z isomerization of the alkenylnickel intermediates enables overall anti-arylmetallative cyclization to occur. The ring system of the products are substructures of certain diarylindolizidine alkaloids. |
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| Keywords: | asymmetric catalysis cyclization isomerization ketones nickel |
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