Enantioselective Synthesis of Chiral Cyclopent‐2‐enones by Nickel‐Catalyzed Desymmetrization of Malonate Esters |
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| Authors: | Dr Somnath Narayan Karad Heena Panchal Christopher Clarke Dr William Lewis Prof Hon Wai Lam |
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| Institution: | 1. http://www.nottingham.ac.uk/～pczhl/;2. The GlaxoSmithKline Carbon Neutral Laboratories for Sustainable Chemistry, University of Nottingham, Jubilee Campus, Nottingham, UK;3. School of Chemistry, University of Nottingham, Nottingham, UK |
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| Abstract: | The enantioselective synthesis of highly functionalized chiral cyclopent‐2‐enones by the reaction of alkynyl malonate esters with arylboronic acids is described. These desymmetrizing arylative cyclizations are catalyzed by a chiral phosphinooxazoline/nickel complex, and cyclization is enabled by the reversible E/Z isomerization of alkenylnickel species. The general methodology is also applicable to the synthesis of 1,6‐dihydropyridin‐3(2H)‐ones. |
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| Keywords: | asymmetric catalysis carbocycles cyclization isomerization nickel |
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