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Enantioselective organocatalytic synthesis of tetrahydroquinolines has been achieved via Saegusa‐type oxidative enamine catalysis/1,5‐hydride transfer/cyclization sequences. The feature of this research is a one‐pot transformation of 3‐aryl aldehydes into tetrahydroquinolines by using environmentally benign catalytic Saegusa oxidation and highly efficient internal redox reactions. The synthetically useful ring‐fused tetrahydroquinoline derivatives were obtained in moderate yields and high levels of enantioselectivity.

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SummaryThe highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes, promoted by binaphthyl-modified chiral bifunctional organocatalysts is described. This reaction afforded the chiral functionalized naphthoquinones in high yields (81–95%) and excellent enantioselectivities (91–98% ee) under low catalyst loading (1 mol %).

The enantioselective conjugate addition reaction of 3-aryl-substituted oxindoles with methyl vinyl ketone promoted by binaphthyl-modified bifunctional organocatalysts was investigated. The corresponding Michael adducts, containing a quaternary center at the C3-position of the oxindoles, were generally obtained in high yields with excellent enantioselectivities (up to 91% ee).

Enantio-and Diastereoselective Michael Addition Reactions of α-Cyanoketones to Nitroalkenes Catalyzed by Binaphthyl-Derived Organocatalyst. -The use of catalyst (I) provides the corresponding γ-nitro α-cyanoketones with excellent diastereo-and enantioselectivity. -(LEE, H. J.; WOO, S. B.; KIM*, D. Y.; Tetrahedron Lett. 53 (2012) 26, 3374-3377, http://dx.

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