178176-80-2

Usage

Uses

Used in Coordination Chemistry:
2-DIPHENYLPHOSPHINO-1-NAPHTHOIC ACID is used as a ligand for stabilizing metal complexes, which is crucial in the development of new catalysts and materials with specific properties.
Used in Catalysis:
In the field of catalysis, 2-DIPHENYLPHOSPHINO-1-NAPHTHOIC ACID is used as a ligand to facilitate organic reactions, enhancing the efficiency and selectivity of chemical processes.
Used in Asymmetric Catalysis:
2-DIPHENYLPHOSPHINO-1-NAPHTHOIC ACID is used as a chiral ligand in asymmetric catalysis, enabling the synthesis of enantiomerically pure compounds, which are essential in pharmaceuticals and agrochemicals.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-DIPHENYLPHOSPHINO-1-NAPHTHOIC ACID is used as a key intermediate in the synthesis of various drugs, contributing to the development of new medications with improved efficacy and selectivity.
Used in Agrochemical Synthesis:
Similarly, in agrochemicals, 2-DIPHENYLPHOSPHINO-1-NAPHTHOIC ACID is used as a component in the synthesis of pesticides and other crop protection agents, helping to create more effective and targeted products.
Used in Fine Chemicals Synthesis:
2-DIPHENYLPHOSPHINO-1-NAPHTHOIC ACID is also used in the synthesis of fine chemicals, which includes a broad range of specialty chemicals used in various industries, from fragrances to high-tech materials. Its versatility makes it an important component in many industrial processes.

InChI:InChI=1/C23H17O2P/c24-23(25)22-20-14-8-7-9-17(20)15-16-21(22)26(18-10-3-1-4-11-18)19-12-5-2-6-13-19/h1-16H,(H,24,25)

Upstream product

• 200573-11-1 1-carbomethoxy-2-(trifluoromethylsulfonyloxy)naphthalene 
• 947-65-9 methyl 2-hydroxy-1-naphthoate 
• 178176-78-8 2-diphenylphosphino-1-naphthoic acid methyl ester 

Downstream Products

• 174810-09-4 (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl) 

Relevant academic research and scientific papers

Dynamic kinetic asymmetric transformation of diene monoepoxides: A practical asymmetric synthesis of vinylglycinol, vigabatrin, and ethambutol

The ability to perform a dynamic kinetic asymmetric transformation (DYKAT) using the palladium-catalyzed asymmetric allylic alkylation (AAA) is explored in the context of butadiene monoepoxide. The versatility of this commercially available, but racemic, four-carbon building block becomes significantly enhanced via conversion of both enantiomers into a single enantiomeric product. The concept is explored in the context of a synthesis of vinylglycinol with phthalimide as the nitrogen source. The success of the project required a new design of the ligand for palladium wherein additional conformational restraints were introduced. Thus, the phthalimide derivative of vinylglycinol was obtained in nearly quantitative yield and had an ee of 98% which, upon crystallization, was enhanced to > 99%. This one-step synthesis of a protected form of vinylglycinol provided short practical syntheses of the title compounds. Vigabatrin requires only four steps, and ethambutol six. The intermediate to the existing synthesis of ethambutol is available in 87% yield in three steps. (R)-Serine derives from oxidative cleavage of the double bond. The reaction of phthalimide and isoprene monoepoxide demonstrates the remarkable ability of the chiral ligands to control both regioselectivity and enantioselectivity and demonstrates the effectiveness of this protocol in creating a quaternary center asymmetrically.

Asymmetric ligands useful for transition metal catalyzed bond forming reactions and epoxide reactions therewith

A novel ligand having the Formula 1 structure has proved remarkably successful in the amination of butadiene monoepoxide, which is a potentially desirable substrate for an asymmetric synthesis providing access to each enantiomer of vinylglycinol. STR1 This and other ligands described are useful for chiral induction of bond forming reactions with an epoxide substrate.

Asymmetric ligands useful for transition metal catalyzed bond forming reactions

Ligands useful for transition metal catalyzed bond forming reactions are provided with a metal binding portion having at least one metal binding moiety STR1 wherein Ar and Ar' each is an aryl or a heteroaryl. These ligands may be prepared by providing an aromatic carboxylic acid having a diarylphosphino or diheteroarylphosphino substituent on the aromatic ring, and forming an ester or an amide derivative of the carboxylic acid by coupling with a chiral diol or a chiral diamine. The ligands facilitate, for example, flexible strategies for enantiocontrolled construction of five membered carbocyclic rings with varying substitution patterns and high enantioselectivity.