Nickel(0)-Catalyzed Enantioselective [3+2] Annulation of Cyclopropenones and α,β-Unsaturated Ketones/Imines

Dachang Bai; Yanjiang Yu; Haiming Guo; Junbiao Chang; Xingwei Li

doi:10.1002/anie.201913130

Nickel(0)-Catalyzed Enantioselective [3+2] Annulation of Cyclopropenones and α,β-Unsaturated Ketones/Imines

Angew Chem Int Ed Engl. 2020 Feb 10;59(7):2740-2744. doi: 10.1002/anie.201913130. Epub 2020 Jan 9.

Authors

Dachang Bai¹, Yanjiang Yu¹, Haiming Guo¹, Junbiao Chang¹, Xingwei Li^{1

2}

Affiliations

¹ Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, China.
² School of Chemistry and Chemical Engineering, Shaanxi Normal University (SNNU), Xi'an, 710062, China.

PMID: 31814239
DOI: 10.1002/anie.201913130

Abstract

Ni⁰ -catalyzed chemo- and enantioselective [3+2] cycloaddition of cyclopropenones and α,β-unsaturated ketones/imines is described. This reaction integrates C-C bond cleavage of cyclopropenones and enantioselective functionalization by carbonyl/imine group, offering a mild approach to γ-alkenyl butenolides and lactams in excellent enantioselectivity (88-98 % ee) through intermolecular C-C activation.

Keywords: cyclopropenones; enantioselective C−C activation; enones; lactones; nickel.

Publication types

Research Support, Non-U.S. Gov't