140834-52-2

Upstream product

• 117582-62-4 1-bromo-2-formyl-3,4-dihydronaphthalene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 127349-02-4 1-bromo-2-(dibromomethyl)naphthalene 
• 2586-62-1 1-bromo-2-methylnaphtalene 
• 3378-82-3 1-bromo-2-naphthaldehyde 
• 20717-79-7 1-bromo-2-naphthoic acid 
• 155998-24-6 1-(2-hydroxy-4,6-dimethylphenyl)-2-naphthaldehyde 
• 138435-72-0 (±)-1,3-dimethyl-6H-benzo[b]naphtho[1,2-d]pyranone 

Relevant academic research and scientific papers

CuH-Catalyzed Atropoenantioselective Reduction of Bringmann's Lactones via Dynamic Kinetic Resolution

A CuH-catalyzed atropoenantioselective reduction of Bringmann's lactones via dynamic kinetic resolution has been disclosed. This protocol features a broad substrate scope and good functional group tolerance and allows the rapid assembly of various valuabl

On the lipase-catalyzed resolution of functionalized biaryls

The implementation of lipase catalysis as a tool for the preparation of optically active biaryls is discussed. While attempts toward dynamic kinetic resolution based on the catalytic ring opening of configurationally unstable biaryl lactones were fruitles

Synthesis and applications of oxaspiro PNN ligand

The invention belongs to the field of chiral synthesis, and specifically provides synthesis of a class of novel oxaspiro PNN ligands. According to the synthesis, oxaspiro diphenol is used as a starting raw material, and trifluoromethyl sulfonylation, palladium-catalyzed diarylphosphine oxide coupling, trichlorosilane reduction, palladium-catalyzed carbon insertion esterification, hydrolysis, amination, reductive amination and other steps are performed to synthesize the novel oxaspiro PNN ligand. According to the present invention, the oxaspiro compound has central chirality, such that the novel oxaspiro PNN ligands comprise the levo-oxaspiro PNN ligand and the dextro-oxaspiro PNN ligand, and the racemic oxaspiro PNN ligand can be synthesized by using the racemic oxaspiro diphenol as the raw material; and the PNN ligand can be used as the chiral ligand for the asymmetric hydrogenation of ketone and lactone, wherein the complex of the ligand and iridium can respectively obtain the enantioselectivity of more than 98% and more than 99% in the asymmetric hydrogenation of simple ketones and lactones.

Atropoenantioselective redox-neutral amination of biaryl compounds through borrowing hydrogen and dynamic kinetic resolution

We report herein a novel atropoenantioselective redox-neutral amination of biaryl compounds triggered by a cascade of borrowing hydrogen and dynamic kinetic resolution under the cooperative catalysis of a chiral iridium complex and an achiral Br?nsted acid. This protocol features broad substrate scope and good functional-group tolerance, and allows the rapid assembly of axially chiral biaryl compounds in good to high yields and with high to excellent enantioselectivity.

Atropoenantioselective Redox-Neutral Amination of Biaryl Compounds through Borrowing Hydrogen and Dynamic Kinetic Resolution

We report herein a novel atropoenantioselective redox-neutral amination of biaryl compounds triggered by a cascade of borrowing hydrogen and dynamic kinetic resolution under the cooperative catalysis of a chiral iridium complex and an achiral Br?nsted acid. This protocol features broad substrate scope and good functional-group tolerance, and allows the rapid assembly of axially chiral biaryl compounds in good to high yields and with high to excellent enantioselectivity.

Ruthenium-Catalyzed Atropoenantioselective Synthesis of Axial Biaryls via Reductive Amination and Dynamic Kinetic Resolution

The unprecedented ruthenium-catalyzed atropoenantioselective reductive amination of aldehydes with alkylamines via a cascade transfer hydrogenation and dynamic kinetic resolution strategy is described. This protocol features broad substrate scope and good functional group tolerance and allows the rapid assembly of axially chiral biaryls in good to high yields with high to excellent enantioselectivities. In addition, such structural motifs may have potential applications in enantioselective catalysis as chiral ligands or catalysts.

Design and Synthesis of Chiral oxa-Spirocyclic Ligands for Ir-Catalyzed Direct Asymmetric Reduction of Bringmann's Lactones with Molecular H2

We herein present a facile and column-free synthetic route toward a structurally unique oxa-spirocyclic diphenol, termed as O-SPINOL. Features of the synthesis include the construction of the all-carbon quaternary center at an early stage, a key double intramolecular SNAr step to introduce the spirocycles and the feasibility of operating on >100 g scale. Both enantiomers of O-SPINOL can be easily accessed through optical resolution with l-proline by control of the solvent. The chiral tridentate ligand O-SpiroPAP derived from O-SPINOL has been successfully synthesized and applied in the iridium-catalyzed asymmetric hydrogenation of bridged biaryl lactones under mild reaction conditions, providing valuable and enantioenriched axially chiral molecules in excellent yields and enantioselectivities (up to 99% yield and >99% ee). This method represents a rare example of constructing axially chiral molecules by direct reduction of esters with H2.

Atropo-enantioselective reduction of configurationally unstable biaryl lactones with BINAL-H1

The atropo-enantioselective reduction of configurationally unstable biaryl lactones with BINAL-H yields axially chiral biaryl alcohols in high enantiomeric ratios of up to 94:6 (er >99.5:0.5 after one crystallization step). Within this two-step reduction

The atropo-enantioselective reduction of configurationally unstable biaryl hydroxy aldehydes - A novel approach to axially chiral biaryls

The oxazaborolidine-assisted atropo-enantioselective catecholborane reduction of configurationally unstable biaryl hydroxy aldehydes to axially chiral biaryl alcohols by (dynamic) kinetic resolution is achieved in enantiomeric ratios (er) of up to 92:8. Using the same chiral auxiliary, the M- or, optionally, the P-configurated atropisomer can be obtained in good er's - just by variation of the relative quantity of the achiral reductant. This hints at the existence of two competing reaction pathways with opposite asymmetric inductions. The enantiomeric ratios observed strongly depend on the relative steric demand of the substituents ortho to the biaryl axis.

Enantioselective addition of diethylzinc to aldehydes using novel axially chiral 2-aminomethyl-1-(2'-hydroxyphenyl)naphthalene catalysts

The synthesis of atropo-enantiomerically pure aminomethyl and hydroxymethyl substituted biaryls derivatives M-2 and M-3 (and, optionally, their enantiomers), by dynamic kinetic resolution of a racemic lactone precursor, is described. Their application as