Enantioselective nickel-catalyzed anti-carbometallative cyclizations of alkynyl electrophiles enabled by reversible alkenylnickel E/Z isomerization

Clarke, Christopher; Incerti-Pradillos, Celia A.; Lam, Hon Wai

Abstract

Nickel-catalyzed additions of arylboronic acids to alkynes, followed by enantioselective cyclizations of the alkenylnickel species onto tethered ketones or enones, are reported. These reactions are reliant upon the formal anti-carbonickelation of the alkyne, which is postulated to occur by the reversible E/Z isomerization of an alkenylnickel species.

Citation

Clarke, C., Incerti-Pradillos, C. A., & Lam, H. W. (2016). Enantioselective nickel-catalyzed anti-carbometallative cyclizations of alkynyl electrophiles enabled by reversible alkenylnickel E/Z isomerization. Journal of the American Chemical Society, 138(26), https://doi.org/10.1021/jacs.6b04206

• Journal Article Type: Article
• Acceptance Date: Jun 11, 2016
• Publication Date: Jun 22, 2016
• Deposit Date: Jul 18, 2016
• Publicly Available Date: Jul 18, 2016
• Journal: Journal of the American Chemical Society
• Print ISSN: 0002-7863
• Electronic ISSN: 1520-5126
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 138
• Issue: 26
• DOI: https://doi.org/10.1021/jacs.6b04206
• Public URL: https://nottingham-repository.worktribe.com/output/793872
• Publisher URL: http://pubs.acs.org/doi/abs/10.1021/jacs.6b04206
• Contract Date: Jul 18, 2016