We describe herein an organocatalytic enantioselective approach for the construction of axially chiral sulfone-containing styrenes. Various styrene compounds were prepared with excellent enantioselectivities (up to >99% ee) and almost complete E/Z selectivities (>99% E/Z). Furthermore, styrenes could be easily converted into phosphonic acid S/P ligands, which potentially used as organocatalysts or ligands in asymmetric catalysis.

A highly diastereo- and enantioselective methodology for the asymmetric synthesis of vicinal diaxial styrenes multiaxis system was achieved by organocatalysis. Various systems were obtained in excellent manners. The mechanism studies revealed that a new tetra-substituted vinylidene ortho-quinone methide (VQM) intermediate likely involved accounted enantioselectivity.

A facile synthesis of imidazo[1,2-α]pyridines has been achieved by copper(II) and iron(III) co-catalyzed C–N bond formation. This reaction involves an intermolecular oxidative diamination alkynes with high chemoselectivity regioselectivity.

A simultaneous asymmetric Mannich reaction and the construction of axially chiral sulfone-containing styrenes in one pot from α-amido sulfones based on waste–reuse strategy was demonstrated. series β-amino diesters with various functional groups were synthesized good to excellent yields enantioselectivities under mild conditions. In addition, this protocol has been successfully applied synthesize anti-HIV drug Maraviroc trichloro derivatives.

Abstract An efficient and concise method for the construction of various O‐glycosidic bonds by a palladium‐catalyzed reaction with 3‐O‐picoloyl glucal has been developed. The stereochemistry anomeric center derives from either an inner‐sphere or outer‐sphere pathway. Harder nucleophiles, such as aliphatic alcohols sodium phenoxides give β‐products, α products result using softer phenol.

A targeting system with excellent ability is constructed by incorporating carbohydrate-modified gold nanoparticles as vehicles and GSH-responsive species the payload.

Structural motifs containing contiguous halide-bearing stereocenters are common in natural products as well bioactive molecules. A few successful examples have been reported the area of asymmetric vicinal dihalogenation alkenes for accessing dihalogenated products; this report, an alternative generation method α,β,γ,δ relative to carbonyl group excellent enantioselectivity is proposed by utilizing a Song's oligoEG catalyst-catalyzed β-elimination. According methodology, wide range...

A chiral fluoride-catalyzed asymmetric cascade sulfa-Michael/aldol condensation reaction of 1,4-dithiane-2,5-diol and a series α,β-unsaturated ketones is described to access trisubstituted tetrahydrothiophene derivatives. The target products, including the spiro derivatives bearing five-, six-, seven-membered ring, were highly functionalized showed high ee value. This established protocol realized enantioselective with catalytic amount KF Song's oligoEG via in situ generated fluoride...

A metal-free protocol for difunctionalization of alkynes through spontaneous selenosulfonylation vinylidene <italic>ortho</italic>-quinone methide (VQM) was developed with good yields and excellent stereoselectivities.

A one-pot dual-organocatalyst-promoted asymmetric α-aminoxylation/aza-Michael/aldol consendation cascade reaction is presented. The targeted optically active 1,2-oxazine derivatives are synthesized in moderate yields (up to 70%), excellent enantioselectivities (ee >99% all cases), and diastereoselectivities (dr up >99:1) under mild conditions. To further elucidate the synthetic utility of products, cleavage N–O bond demonstrated an enantiopure syn-1,4-amino alcohol derivative achieved yield.

We describe herein the first enantioselective organocatalytic Michael addition reaction of α-amido sulfones to ynones access axially chiral styrenes.

Abstract cis ‐2,6‐Tetrahydropyran is an important structural skeleton of bioactive natural products. A facile synthesis ‐2,6‐disubstituted‐3,6‐dihydropyrans as ‐2,6‐tetrahydropyran precursors has been achieved in high regio‐ and stereoselectivity with yields. This reaction involves a palladium‐catalyzed decarboxylative allylation various 3,4‐dihydro‐2 H ‐pyran substrates. Extending this to 1,2‐unsaturated carbohydrates allowed the achievement challenging β‐C‐glycosylation. Based on...

A highly efficient cascade process of Michael–aza-Henry–hemiaminalization–dehydration was established for the construction enantiopure tetrahydropyridines using combination prolinol trimethylsilyl ether and cinchona alkaloid catalysts. This new approach allowed application aliphatic imines, generated in situ from aldehydes amines. Good yields (up to 90%), high enantio- >99% ee) diastereoselectivities (>99 : 1 d.r. all cases) were achieved a broad spectrum substrates under mild conditions.

The Pd-π-allyl intermediate in an electron-rich glycal system with poor reactivity is employed as efficient glycosyl donor. Starting from glucal derived carbonate, various O-glycosides were formed via a palladium-catalyzed reaction through tandem decarboxylation, proton abstraction, and nucleophilic addition, good yields excellent selectivity. Iterative glycosylation the same strategy may provide access to complex oligosaccharides.

Abstract In this study, the concept of cooperative cation‐binding catalysis was applied for direct generation two contiguous trisubstituted and tetrasubstituted stereogenic centers. Using readily accessible chiral oligoethylene glycol (oligoEG) as a catalyst, asymmetric Mannich reactions α‐thiocyanato cyclic ketones donors were performed with α‐amidosulfones bench‐stable imine precursors in presence potassium fluoride base, affording 2‐thiocyanato‐2‐(1‐aminoalkyl)‐substituted 1‐tetralones...

An organocatalytic cascade reaction was established for the construction of indoloquinolizidine derivatives bearing five contiguous stereocenters from readily available starting materials.

Asymmetric cation-binding catalysis, in principle, can generate "chiral" anionic nucleophiles, where the counter cations are coordinated within chiral environments. Nitrogen nucleophiles intrinsically basic, therefore, its use as is often challenging and limiting scope of reaction. Particularly, a formation configurationally labile aminal centers with alkyl substituents has been formidable challenge due to enamine/imine equilibrium electrophilic substrates. Herein, we report enantioselective...

A Michael-Mannich-hemiaminalization-dehydration cascade reaction was developed for the construction of spirooxindole benzoquinolizine derivatives. Additionally, benzoindolizidine prepared conveniently through a ring-contracted rearrangement from benzoquinolizine.

An unprecedented highly diastereoselective dimerization of 2-alkynylnaphthols is presented to furnish bridged polycyclic compounds containing a bicyclo[3.2.1]octane moiety with good excellent yields. The reaction proceeded under mild conditions using N-iodosuccinimide as promoter, simultaneously constructing one new C–O bond and two C–C bonds. A tetra-substituted vinylidene ortho-quinone methide intermediate was likely involved, the steric hindrance substituents played critical role in this...

A highly efficient approach to the construction of indolizidines and quinolizidines bearing a bridged quaternary stereocenter has been established in one-pot fashion using aldehydes, nitroalkenes, cyclic ketimines.

Abstract An efficient and concise method for the construction of various O‐glycosidic bonds by a palladium‐catalyzed reaction with 3‐O‐picoloyl glucal has been developed. The stereochemistry anomeric center derives from either an inner‐sphere or outer‐sphere pathway. Harder nucleophiles, such as aliphatic alcohols sodium phenoxides give β‐products, α products result using softer phenol.