Shou-Guo Wang

Ring-closing metathesis/isomerization/Pictet-Spengler cascade via ruthenium/chiral phosphoric acid sequential catalysis.

Chiral phosphoric acid worked together with Hoveyda-Grubbs II catalyst enabling highly efficient synthesis of enantioenriched tetrahydro-β-carbolines (up to 98% yield, 99% ee) through a ring-closing metathesis/isomerization/Pictet-Spengler cascade reaction via sequential catalysis.

Asymmetric Dearomatization of β-Naphthols through an Amination Reaction Catalyzed by a Chiral Phosphoric Acid†

A highly efficient catalytic asymmetric dearomatization of naphthols by means of an electrophilic amination reaction catalyzed by chiral phosphoric acid is presented. This protocol provides a facile access to functionalized β-naphthalenone compounds with a chiral quaternary carbon center in excellent yields and enantioselectivity (up to 99% yield, up to 96% ee).

Asymmetric synthesis of tetrahydro-β-carbolines via chiral phosphoric acid catalyzed transfer hydrogenation reaction.

Chiral phosphoric acid catalyzed enantioselective transfer hydrogenation of hydroxylactams has been realized to provide enantioenriched tetrahydro-β-carbolines in dioxane at room temperature (up to 94% yield, 90% ee).

Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction

An intermolecular asymmetric dearomatization reaction of β-naphthols with nitroethylene through a chiral-thiourea-catalyzed Michael reaction is described. Enantioenriched functionalized β-naphthalenones with an all-carbon quaternary stereogenic center could thus be easily constructed from simple naphthol derivatives in good yields and excellent enantioselectivity (up to 79% yield, 98% ee).

Construction of spiro-tetrahydroquinolines via intramolecular dearomatization of quinolines: free of a preinstalled activation group.

A highly efficient synthesis of spiro-tetrahydroquinolines (up to 99% yield) has been realized via cascade hydrogenative dearomatization of quinoline and intramolecular aza-Friedel-Crafts alkylation reaction.

N-alkylation of indole via ring-closing metathesis/isomerization/Mannich cascade under ruthenium/chiral phosphoric acid sequential catalysis

A sequential catalysis by combining the Zhan-1B catalyst with chiral phosphoric acid has been utilized for N-alkylation of indole through a ring-closing metathesis/double bond isomerization/Mannich reaction cascade. Enantioenriched γ-lactams were synthesized in up to 92% yield and 95% ee.

Palladium(0)‐Catalyzed Intermolecular Arylative Dearomatization of β‐Naphthols

The first Pd0 -catalyzed intermolecular arylative dearomatization of β-naphthols with aryl halides is described. It was found that Q-Phos could facilitate the palladium-catalyzed cross-coupling-type dearomatization of β-naphthols, while avoiding O-arylation, to construct 2-naphthalenones in excellent yields and with high chemoselectivity.

Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet–Spengler Reaction of Indolyl Dihydropyridines

A highly efficient synthesis of the enantioenriched tetrahydro-β-carbolines was developed by using a chiral phosphoric acid catalyzed Pictet-Spengler reaction of indolyl dihydropyridines. The reaction proceeds under mild reaction conditions to afford the desired chiral tetrahydro-β-carbolines in good to excellent yields (up to 96 %) and high enantioselectivities (up to 99 % ee). With this method, a formal synthesis of tangutorine and a total synthesis of deplancheine were achieved in a highly efficient manner.