Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters

Karad, Somnath Narayan and Panchal, Heena and Clarke, Christopher and Lewis, William and Lam, Hon Wai (2018) Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters. Angewandte Chemie International Edition, 57 (29). pp. 9122-9125. ISSN 1433-7851

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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.

Item Type: Article
Keywords: asymmetric catalysis; carbocycles; cyclization; isomerization; nickel
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: https://doi.org/10.1002/anie.201805578
Depositing User: Eprints, Support
Date Deposited: 28 Aug 2018 10:17
Last Modified: 19 Jun 2019 04:30
URI: http://eprints.nottingham.ac.uk/id/eprint/53504

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