A series of Schiff-based ligands consisting of both tertiary amines and lipophilic groups were designed and synthesized. Using these ligands, a new chiral surfactant-type metallomicellar catalyst was developed in water, and this was identified by SEM/TEM analyses. These metallomicelles can be empolyed in asymmetric Michael addition reactions in water, delivering the corresponding adducts with excellent yields and enantioselectivities.

Highly enantioselective Friedel–Crafts alkylation of pyrroles with 2-enoyl-pyridine N-oxides in water/chloroform (10:1) was developed under catalysis of Lewis acid. The Friedel–Crafts alkylation products can be obtained in high yields and excellent enantioselectivities. Moreover, several control experiments were carried out to study the reaction mechanism.

A highly enantioselective Mukaiyama aldol reaction of silyl enol ethers with isatins catalyzed by chiral copper complexes was developed. A series of chiral 3-substituted 3-hydroxy-2-oxindoles bearing a tetra-substituted center could be obtained exclusively with high yields (up to 95%) and excellent enantioselectivities (up to 99%). In particular, water was essential to improve the diastereoselectivity.

A highly enantioselective Michael addition of nitro esters to 2-enoyl-pyridine N-oxides was developed by using chiral copper catalysts. The Michael addition products can be obtained in high yields and with up to 96% ee. Moreover, asymmetric Michael addition product of nitromethane to 2-enoyl-pyridine N-oxides can be obtained in one step. An analogue of nicotine, dihydro-2H-pyrrol 4b was synthesized with this developed method.

A chiral C–O bond delivering chiral N,O-ketals was developed via an organocatalytic dehydration/aminalization/aza-Michael desymmetrization.

A new water-soluble catalytic system was developed and used in an enantioselective Michael addition of pyrroles with nitroalkenes in water to afford nitroethylpyrrole derivatives with both excellent yields and ee values.

A highly enantioselective Henry reaction of β,γ-unsaturated α-ketoesters with nitromethane in water by virtue of chiral copper complexes has been developed. A series of unsaturated β-nitro-α-hydroxy esters bearing tetrasubstituted carbon stereocenters were obtained exclusively with high yields and excellent enantioselectivities. This method could avoid tedious anaerobic anhydrous manipulation and reduce the environmental pollution caused by organic solvents.

A one-pot protocol has been developed for sequential benzyne activation and nucleophilic substitution of enantioenriched tertiary benzylic amines. In the presence of 2 (trimethylsilyl)phenyl triflate and CsF, a range-of enantioen-riched tertiary benzylic amines were substituted by various nucleophiles, delivering structurally diverse benzylic-compounds in moderate to excellent yields with excellent retention of enantiopurity. Importantly, this operationally simple protocol permitted formation of various chiral C-S, C-Se, C-C, and C-N bonds with excellent enantiopurity under metal-free conditions.

A by-product-catalyzed redox-neutral process has been established through tandem sulfenylation/deiodination/aromatization of cyclic alkenyl iodides with sulfonyl hydrazides. In the absence of external catalysts and additives a range of 4-iodo-1,2-dihydronaphthalenes reacted with sulfonyl hydrazides to give structurally diverse 2-naphthyl thioethers in good yields. Mechanistic studies showed that at an early stage sulfonyl hydrazides decomposed completely to thiosulfonates and disulfides and at a late stage the resulting thiosulfonates underwent tandem sulfenylation/deiodination/aromatization with 4-iodo-1,2-dihydronaphthalenes involving a [1,5]-sigmatropic hydrogen shift. Importantly, iodine was generated as a by-product from 4-iodo-1,2-dihydronaphthalenes upon heating and served as a catalyst for the decomposition of sulfonyl hydrazides and subsequent formation of 2-naphthyl thioethers.