Nickel-Catalyzed Asymmetric Domino Ring Opening/Cross-Coupling Reaction of Cyclobutanones via a Reductive Strategy

• Published in: iScience Vol. 23; no. 4; p. 101017
• Main Authors: Ding, Decai, Dong, Haiyan, Wang, Chuan
• Format: Journal Article
• Language: English
• Published: United States Elsevier Inc 24.04.2020; Elsevier
• Subjects: Catalysis; Organic Reaction; Organic Synthesis; Organic Reaction; Organic Synthesis; Catalysis
• ISSN: 2589-0042; 2589-0042
• DOI: 10.1016/j.isci.2020.101017

Herein we demonstrate the successful application of reductive strategy in the asymmetric domino ring opening/cross-coupling reaction of prochiral cyclobutanones. Under the catalysis of a chiral nickel complex, various aryl iodide-tethered cyclobutanones were reacted with alkyl bromides as the electrophilic coupling partner, providing a variety of chiral indanones bearing a quaternary stereogenic center in highly enantioselective manner, which can be further converted to diverse benzene-fused cyclic compounds including indane, indene, dihydrocoumarin, and dihydroquinolinone. The preliminary mechanistic investigations support a mechanism involving Ni(I)-mediated enantiotopic C−C σ-bond activation of cyclobutanones as key elementary step in the catalytic cycle. [Display omitted] •Asymmetric ring opening of prochiralcyclobutanones via reductive Nickel-catalysis•Merger of electrophilic ring opening and cross-electrophile coupling•Chiral indanones were synthesized in highly enantioselective manner Catalysis; Organic Synthesis; Organic Reaction