Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of 2‑Substituted 2,3-Dihydro-4-quinolones by a Protecting-Group-Free Approach

Chiral 2-substituted 2,3-dihydro-4-quinolones were synthesized based on the chiral phosphoric acid catalyzed intramolecular aza-Michael addition reaction using N-unprotected 2-aminophenyl vinyl ketones as substrates in good yields with high enantioselectivities

Chiral Phosphoric Acid Catalyzed Enantioselective Transfer Deuteration of Ketimines by Use of Benzothiazoline As a Deuterium Donor: Synthesis of Optically Active Deuterated Amines

By use of 2-deuterated benzothiazoline as a deuterium donor in combination with a chiral phosphoric acid, the transfer deuteration of ketimine and α-iminoester took place smoothly to give α-deuterated amines in high yields with excellent enantioselectivities. The remarkable kinetic isotope effect suggests that carbon–deuterium bond cleavage is the rate-determining step

Chiral Phosphoric Acid Catalyzed Enantioselective Transfer Deuteration of Ketimines by Use of Benzothiazoline As a Deuterium Donor: Synthesis of Optically Active Deuterated Amines

By use of 2-deuterated benzothiazoline as a deuterium donor in combination with a chiral phosphoric acid, the transfer deuteration of ketimine and α-iminoester took place smoothly to give α-deuterated amines in high yields with excellent enantioselectivities. The remarkable kinetic isotope effect suggests that carbon–deuterium bond cleavage is the rate-determining step

Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed C(sp³)–H Bond Functionalization and Its Application to Formal Synthesis of (±)-Tetrahydropalmatine

An expeditious route to furnish an isoquinoline skeleton via hydride shift mediated C–H bond functionalization was developed. In this process, an unusual [1,5]-H shift without the assistance of the adjacent heteroatom took place to produce tetrahydroisoquinoline derivatives in good to excellent chemical yields. The formal synthesis of (±)-tetrahydropalmatine was achieved by exploiting this new transformation

Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed C(sp³)–H Bond Functionalization and Its Application to Formal Synthesis of (±)-Tetrahydropalmatine

An expeditious route to furnish an isoquinoline skeleton via hydride shift mediated C–H bond functionalization was developed. In this process, an unusual [1,5]-H shift without the assistance of the adjacent heteroatom took place to produce tetrahydroisoquinoline derivatives in good to excellent chemical yields. The formal synthesis of (±)-tetrahydropalmatine was achieved by exploiting this new transformation

B(C₆F₅)₃‑Catalyzed Hydrodesulfurization Using Hydrosilanes – Metal-Free Reduction of Sulfides

B­(C₆F₅)₃-catalyzed hydrodesulfurization of carbon–sulfur bonds was achieved using triethylsilane as the reducing agent. The corresponding products were obtained in good yields under mild reaction conditions. This protocol could be applied to the reduction of sulfides, including benzyl and alkyl sulfides and dithianes, with high chemoselectivities

Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed C(sp³)–H Bond Functionalization and Its Application to Formal Synthesis of (±)-Tetrahydropalmatine

An expeditious route to furnish an isoquinoline skeleton via hydride shift mediated C–H bond functionalization was developed. In this process, an unusual [1,5]-H shift without the assistance of the adjacent heteroatom took place to produce tetrahydroisoquinoline derivatives in good to excellent chemical yields. The formal synthesis of (±)-tetrahydropalmatine was achieved by exploiting this new transformation

Chiral Phosphoric Acid-Catalyzed Oxidative Kinetic Resolution of Indolines Based on Transfer Hydrogenation to Imines

The oxidative kinetic resolution of 2-substituted indoline derivatives was achieved by hydrogen transfer to imines by means of a chiral phosphoric acid catalyst. The oxidative kinetic resolution was applicable to racemic alkyl- or aryl-substituted indolines, and the remaining indolines were obtained in good yields with excellent enantioselectivities

Chiral Magnesium Bisphosphate-Catalyzed Asymmetric Double C(sp³)–H Bond Functionalization Based on Sequential Hydride Shift/Cyclization Process

Described herein is a chiral magnesium bisphosphate-catalyzed asymmetric double C­(sp³)–H bond functionalization triggered by a sequential hydride shift/​cyclization process. This reaction consists of stereo­selective domino C­(sp³)–H bond functionalization: (1) a highly enantio- and diastereo­selective C­(sp³)–H bond functionalization by chiral magnesium bisphosphate (first [1,5]-hydride shift), and (2) a highly diastereo­selective C­(sp³)–H bond functionalization by an achiral catalyst (Yb­(OTf)₃, second [1,5]-hydride shift)

Chiral Magnesium Bisphosphate-Catalyzed Asymmetric Double C(sp³)–H Bond Functionalization Based on Sequential Hydride Shift/Cyclization Process

Described herein is a chiral magnesium bisphosphate-catalyzed asymmetric double C­(sp³)–H bond functionalization triggered by a sequential hydride shift/​cyclization process. This reaction consists of stereo­selective domino C­(sp³)–H bond functionalization: (1) a highly enantio- and diastereo­selective C­(sp³)–H bond functionalization by chiral magnesium bisphosphate (first [1,5]-hydride shift), and (2) a highly diastereo­selective C­(sp³)–H bond functionalization by an achiral catalyst (Yb­(OTf)₃, second [1,5]-hydride shift)