828927-94-2

Usage

Reaction

The PINAP family of P,N ligands is a synthetically more accessible but a similarly performing analog of the QUINAP (15-1777, 15-1778) ligand in enantioselective hydroboration, alkyne addition, and azomethine cycloaddition reactions. With rhodium, enantioselective hydroboration of alkenes as a route to chiral alcohols. With silver, catalytic, enantioselective, azomethine cycloaddition with acrylates.

Upstream product

• 829-85-6 diphenylphosphane 
• 828300-88-5 (R)-trifluoromethanesulfonic acid 1-(4-(1-phenylethoxy)phthalazin-1-yl)-naphthalen-2-yl ester 
• 135-19-3 β-naphthol 
• 828300-87-4 (R)-1-(4-(1-phenylethoxy)phthalazin-1-yl)-naphthalen-2-ol 
• 597552-98-2 1-(4-chlorophthalazin-1-yl)-naphthalen-2-ol 
• 4752-10-7 1,4-dichlorophthalazine 

Relevant academic research and scientific papers

Atroposelective Synthesis of PINAP via Dynamic Kinetic Asymmetric Transformation

The atroposelective synthesis of PINAP ligands has been accomplished via a palladium-catalyzed C?P coupling process through dynamic kinetic asymmetric transformation. These catalytic conditions allow access to a wide variety of alkoxy- and benzyloxy-substituted PINAP ligands in high enantiomeric excess. The methods described in this communication afford valuable P,N ligands in good yields and high enantioselectivity using low catalyst loading. (Figure presented.).

Monophosphine compound, transition metal complex thereof and production method of optically active compound using the complex as asymmetric catalyst

The present invention provides a compound represented by the formula (I): wherein ring A is void or a benzene ring optionally having substituent(s), R1 and R2 are each independently a phenyl group optionally having substituent(s), a cyclohexyl group and the like, R3 and R4 are each independently a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group and the like, and X is a residue represented by —OR5 or —NHR6 wherein R5 and R6 are a lower alkyl group optionally having substituent(s), an aralkyl group optionally having substituent(s) and the like, a asymmetric transition metal complex containing the compound as a ligand and a production method of optically active compound using the complex as an asymmetric catalyst.

Readily available biaryl P,N ligands for asymmetric catalysis

A short and modular synthesis of novel P,N ligands (pinap; see scheme; X = O or NH) is presented. A covalently bound chiral group allows the separation of the atropisomeric diastereomers, thus avoiding resolution involving chiral Pd-amine complexes. The utility of the ligands is demonstrated for three reactions catalyzed by different transition metals; in each case products are obtained with high enantiomeric excess (up to 99% ee).