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Enantioselective Nickel-Catalyzed Intramolecular Allylic Alkenylations Enabled by Reversible Alkenylnickel E/Z Isomerization |
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| Authors: | Connor Yap Dr Gabriel M J Lenagh-Snow Dr Somnath Narayan Karad Dr William Lewis Dr Louis J Diorazio Prof Hon Wai Lam |
| Institution: | 1. The GSK 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;3. The GSK Carbon Neutral Laboratories for Sustainable Chemistry, University of Nottingham, Jubilee Campus, Triumph Road, Nottingham, NG7 2TU UK
School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD UK;4. AstraZeneca, Pharmaceutical Technology and Development, Etherow F53/20, Charter Way, Macclesfield, Cheshire, SK10 2NA UK |
| Abstract: | Enantioselective nickel-catalyzed arylative cyclizations of substrates containing a Z-allylic phosphate tethered to an alkyne are described. These reactions give multisubstituted chiral aza- and carbocycles, and are initiated by the addition of an arylboronic acid to the alkyne, followed by cyclization of the resulting alkenylnickel species onto the allylic phosphate. The reversible E/Z isomerization of the alkenylnickel species is essential for the success of the reactions. |
| Keywords: | allylic substitution asymmetric catalysis cyclization isomerization nickel |