Diastereodivergent Catalytic Asymmetric Michael Addition of 2-Oxindoles to α,ß-Unsaturated Ketones by Chiral Diamine Catalysts.

A diastereodivergent catalytic asymmetric Michael addition of 2-oxindoles to α,ß-unsaturated ketones has been successfully developed with two complementary chiral diamine catalysts, affording chiral 3,3-disubstituted oxindoles with two adjacent chiral centers. Diastereodivergence has been realized through modifying substrates and utilizing different catalysts. Either anti-or syn-configured products possessing vicinal quaternary and tertiary stereogenic centers were produced with high enantioselectivities.

Enantioselective organocatalytic phospha-Michael reaction of alpha,beta-unsaturated ketones.

Enantioselective organocatalytic phospha-Michael reaction of alpha,beta-unsaturated ketones and diaryl phosphine oxides has been developed for the first time employing multifunctional organocatalysts. Optically active products bearing quaternary chiral carbon stereocenters were obtained in high yields with good to excellent enantioselectivities (up to 98% ee).

Enantioselective Michael addition of ketones to maleimides catalyzed by bifunctional monosulfonyl DPEN salt.

An unprecedented enantioselective Michael addition of various ketones to maleimides catalyzed by a simple bifunctional primary amine, monosulfonyl DPEN salt, is reported and provides the desired adducts in good to excellent yields (up to 99%) with excellent enantioselectivities (up to 99%).

Enantioselective organocatalytic michael addition of malonates to alpha,beta-unsaturated ketones.

A novel type of primary amine thiourea organocatalysts derived from 1,2-diaminocyclohexane and 9-amino (9-deoxy) cinchona alkaloid was developed into asymmetric Michael addition of malonates to enones. A series of cyclic and acyclic enones could react very well with different malonates in the presence of 4 with 0.5-10 mol % catalyst loading affording chiral Michael adducts with excellent yields and ee values.