Asymmetric Hydrogenation of In†Situ Generated Isochromenylium Intermediates by Copper/Ruthenium Tandem Catalysis.

ABSTRACT

The first asymmetric hydrogenation of in situ generated isochromenylium derivatives is enabled by tandem catalysis with a binary system consisting of Cu(OTf)2 and a chiral cationic ruthenium-diamine complex. A range of chiral 1H-isochromenes were obtained in high yields with good to excellent enantioselectivity. These chiral 1H-isochromenes could be easily transformed into isochromanes, which represent an important structural motif in natural products and biologically active compounds. The chiral induction was rationalized by density functional theory calculations.