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

Karad, Somnath Narayan; Panchal, Heena; Clarke, Christopher; Lewis, William; Lam, Hon Wai

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.

Citation

Karad, S. N., Panchal, H., Clarke, C., Lewis, W., & Lam, H. W. (2018). Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters. Angewandte Chemie International Edition, 57(29), 9122-9125. https://doi.org/10.1002/anie.201805578

• Journal Article Type: Article
• Acceptance Date: May 16, 2018
• Online Publication Date: Jun 19, 2018
• Publication Date: Jul 16, 2018
• Deposit Date: Aug 2, 2018
• Publicly Available Date: Jun 19, 2019
• Journal: Angewandte Chemie International Edition
• Print ISSN: 1433-7851
• Electronic ISSN: 1521-3773
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 57
• Issue: 29
• Pages: 9122-9125
• DOI: https://doi.org/10.1002/anie.201805578
• Keywords: Asymmetric catalysis; Carbocycles; Cyclization; Isomerization; Nickel
• Public URL: https://nottingham-repository.worktribe.com/output/914820
• Publisher URL: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201805578
• Contract Date: Aug 31, 2018