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Asymmetric Three-Component Coupling Reaction of Alkyne, Enone, and Aldehyde Catalyzed by Chiral Phebox Ruthenium Catalysts

Author:
Ubukata, Shino, Ito, Jun-ichi, Oguri, Ryota, Nishiyama, Hisao
Source:
Journal of organic chemistry 2016 v.81 no.8 pp. 3347-3355
ISSN:
1520-6904
Subject:
X-radiation, aldehydes, alkynes, catalysts, chemical reactions, ketones, ligands, moieties, organic chemistry, ruthenium
Abstract:
Catalytic asymmetric three-component coupling reactions of terminal alkynes, α,β-unsaturated ketones, and aldehydes were studied. The chiral ruthenium complexes containing bis(oxazolinyl)phenyl ligands were found to serve as efficient catalysts for a tandem reaction based on conjugate addition of terminal alkynes to α,β-unsaturated ketones and subsequent aldol reaction with aldehydes, giving β-hydroxyketone derivatives containing α-propargyl groups in high yields with moderate to good enantioselectivities. This method can produce various functional molecules from commercially available substrates in a one-pot procedure. The absolute configuration of the major product was determined by X-ray analysis. The control experiments suggested that a ruthenium enolate species generated in situ by conjugate addition could be involved as an intermediate for the aldol coupling with an aldehyde.
Agid:
5506157