174810-09-4

Basic information

• Product Name: (1R,2R)-(+)-1,2-DIAMINOCYCLOHEXANE-N,N'-BIS(2-DIPHENYLPHOSPHINO-1-NAPHTHOYL)
• Synonyms: (1R,2R)-(+)-1,2-DIAMINOCYCLOHEXANE-N,N'-BIS(2-DIPHENYLPHOSPHINO-1-NAPHTHOYL);(R,R)-TROST LIGAND(NAPHTHYL);(1R,2R)-(+)-1,2-Diaminocyclohexane-N,N'-bis(2-diphenylphosphino-1-naphthoyl),min.94%(R,R)-DACH-NaphthylTrostLigand;(R,R)-DACH-naphthyl Trost ligand;(1R,2R)-(-)-1,2-Diaminocyclohexane-N,N'-bis(2-diphenylphosphino-1-naphthoyl),94%;(1R,2R)-(+)-1,2-DiaMinocyclohexane-N,N'-bis(2-diphenylphosphino-1-naphthoyl),94% (R,R)-DACH-Naphthyl Trost Ligand;(1R,2R)-(+)-1,2-DiaMinocyclohexane-N,N'-bis(2-diphenylphosphino-1-naphthoyl),(R,R)-DACH-Naphthyl Trost Ligand;N,N'-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthaMide)
• CAS NO: 174810-09-4
• Molecular Formula: C₅₂H₄₄N₂O₂P₂
• Molecular Weight: 790.87
• Product Categories: Chiral Nitrogen;DACH&Trost Series
• Mol File: 174810-09-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 224-231 °C
• Appearance: off-white/Powder
• PKA: 13.43±0.40(Predicted)
• CAS DataBase Reference: (1R,2R)-(+)-1,2-DIAMINOCYCLOHEXANE-N,N'-BIS(2-DIPHENYLPHOSPHINO-1-NAPHTHOYL)(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-(+)-1,2-DIAMINOCYCLOHEXANE-N,N'-BIS(2-DIPHENYLPHOSPHINO-1-NAPHTHOYL)(174810-09-4)
• EPA Substance Registry System: (1R,2R)-(+)-1,2-DIAMINOCYCLOHEXANE-N,N'-BIS(2-DIPHENYLPHOSPHINO-1-NAPHTHOYL)(174810-09-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 174810-09-4(Hazardous Substances Data)

Usage

Reactions

The palladium complexes of the Trost ligands are effective in a variety of allylic substitution reactions involving carbon, nitrogen, oxygen, and fluorides nucleophiles.

Chemical Properties

white to off-white powder

Uses

Trost Ligands for Asymmetric Allylic Alkylation

Upstream product

• 205495-66-5 1,2-diaminocyclohexane-N,N'-bis(2'-diphenylphosphonium-1-naphthoyl) 
• 200573-11-1 1-carbomethoxy-2-(trifluoromethylsulfonyloxy)naphthalene 
• 178176-78-8 2-diphenylphosphino-1-naphthoic acid methyl ester 
• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 178176-80-2 2-diphenylphosphino-1-naphthanoic acid 
• 947-65-9 methyl 2-hydroxy-1-naphthoate 

Relevant articles and documents

Preparation method of chiral Trost ligand

The invention relates to a preparation method of a chiral Trost ligand. The preparation method of the chiral Trost ligand comprises the following steps: mixing a solvent and a racemic Trost ligand toprepare a pretreatment solution; allowing the pretreatment liquid to flow into an adsorbent for adsorption treatment and then flow out, heating obtained effluent to 40 DEG C to 120 DEG C for heat treatment, conducting cooling, then performing adsorption treatment, and repeating the above cycle; after circulation is finished, collecting the adsorbent, conducting eluting with an eluent, and collecting eluate, wherein the adsorbent is macroporous resin. According to the preparation method, the R,R-configuration Trost ligand with an ee value higher than 99% can be prepared. Meanwhile, the preparation method of the chiral Trost ligand is simple in step and high in production efficiency, and can effectively avoid the wasting of S,S-configuration Trost ligands.

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.