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

作者：Ubukata Shino; Ito Jun ichi^*; Oguri Ryota; Nishiyama Hisao^*

来源：Journal of Organic Chemistry, 2016, 81(8): 3347-3355.

DOI：10.1021/acs.joc.6b00374

Catalytic asymmetric three-component coupling reactions of terminal alkynes, alpha,beta-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 alpha,beta-unsaturated ketones and subsequent aldol reaction with aldehydes, giving beta-hydroxyketone derivatives containing a-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.

• 出版日期2016-4-15