Highly efficient asymmetric synthesis of α,ß-epoxy esters via one-pot organocatalytic epoxidation and oxidative esterification.

Highly enantioselective synthesis of α,ß-epoxy esters was achieved via one-pot organocatalytic epoxidation and consequent oxidative esterification. Excellent enantioselectivities (up to 99% ee) and good yields were obtained for a variety of α,ß-epoxy esters. The method was readily scaled. Furthermore the product was applied towards the synthesis of (-)-clausenamide with excellent enantioselectivities (>99% ee).

An organocatalytic cascade reaction of 2-nitrocyclohexanone and α,ß-unsaturated aldehydes with unusual regioselectivity.

An organocatalytic cascade reaction of 2-nitrocyclohexanone and α,ß-unsaturated aldehydes was developed. Bicyclo[3.3.1]nonanone products were obtained with good yields and excellent enantioselectivities. The reaction occurred with unusual regioselectivity. A dienolate-iminium activation mechanism was proposed. The products were transformed to eight-membered cyclic ketones with high enantioselectivity.

Highly enantioselective synthesis of nitrocyclopropanes via organocatalytic conjugate addition of bromomalonate to alpha,beta-unsaturated nitroalkenes.

Highly enantioselective synthesis of nitrocyclopropanes was achieved via the organocatalytic conjugate addition of dimethyl bromomalonate to nitroalkenes and the consequent intramolecular cyclopropanation. 6'-Demethyl quinine was found to be the efficient catalyst. Excellent enantioselectivities, diastereoselectivities, and good yields were obtained for a variety of aryl or heteroaryl nitroethylenes.