866081-62-1 Usage
Reaction
Ligand for the rhodium-catalyzed, asymmetric hydrogenation of dehydroamino acid esters and α-enamides.
Ligand for the rhodium-catalyzed, asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds.
Ligand for the rhodium-catalyzed, asymmetric alkylative ring opening reaction
Ligand for the palladium-catalyzed asymmetric allylic alkylation and amination of racemic substrates.
Ligand for the ruthenium-catalyzed asymmetric hydrogenation of ketones.
Ligand for the rhodium-catalyzed, asymmetric hydroacylation of 1,1-disubstituted alkenes with aldehydes.
Ligand for the silver-catalyzed asymmetric nitroso aldol reaction.
Cu-catalyzed enantioconvergent allyllic borylation.
Cu-catalyzed enantioselective cyclopropylation.
Description
(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline is an efficient ligand exhibiting high levels of enantiocontrol in synthetic transformations ranging from metal-catalyzed 1,4-addition of arylboronic acids to asymmetric hydrogenation to alkylative ring opening.
Uses
Air-Stable and Highly Efficient Chiral Ligands
Application
Air-Stable and Highly Efficient Chiral Ligands,Efficient ligand exhibiting high levels of enantiocontrol in synthetic transformations ranging from metal-catalyzed 1,4-addition of arylboronic acids to alkylative ring opening to asymmetric hydrogenation.
General Description
(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline is an air-stable C2-symmetric P-stereogenic phosphine ligand.
Synthesis
In 4 ml of tetrahydrofuran was dissolved 236 mg (2.0 mmol) of (R)-tert-butylmethylphosphine-borane (9), and the resulting solution was cooled to -78° C. with liquid nitrogen. To the cooled solution was added dropwise 1.25 ml of a 1.6 M hexane solution of n-butyllithium. Fifteen minutes later, a solution of 133 mg (0.67 mmol) of 2,3-dichloroquinoxaline (10) in 4 ml of tetrahydrofuran was added thereto dropwise while vigorously stirring to form a diphosphine-borane compound (11) as an intermediate. The liquid temperature was raised to room temperature over one hour, at which the mixture was stirred for 3 hours. One milliliter of TMEDA was added thereto, and the stirring was continued for an additional 2 hour period to complete deboranation. The reaction was ceased by addition of 1M hydrochloric acid. The reaction mixture was extracted with hexane. The extract was washed successively with 1M hydrochloric acid and a saturated sodium chloride aqueous solution and dried over sodium sulfate. The solvent was removed by evacuation, and the residue was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=30/1) to give (R,R)-2,3-bis(tert-butylmethylphosphino)quinoxaline (12) as an orange solid. Recrystallization from 1.7 ml of hot methanol gave orange crystals (>99% ee) in a yield of 80%.
Check Digit Verification of cas no
The CAS Registry Mumber 866081-62-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,6,6,0,8 and 1 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 866081-62:
(8*8)+(7*6)+(6*6)+(5*0)+(4*8)+(3*1)+(2*6)+(1*2)=191
191 % 10 = 1
So 866081-62-1 is a valid CAS Registry Number.
InChI:InChI=1/C18H28N2P2/c1-17(2,3)21(7)15-16(22(8)18(4,5)6)20-14-12-10-9-11-13(14)19-15/h9-12H,1-8H3
866081-62-1Relevant articles and documents
METHOD FOR PRODUCING 2,3-BISPHOSPHINOPYRAZINE DERIVATIVE, AND METHOD FOR PRODUCING PHOSPHINE TRANSITION METAL COMPLEX
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Paragraph 0087-0093, (2020/08/20)
There is provided a method for producing a 2,3-bisphosphinopyrazine derivative, the method comprising a first step of adding a base to a liquid comprising: 2,3-dihalogenopyrazine represented by the following general formula (1); a hydrogen-phosphine borane compound represented by the following general formula (2); and a deboranating agent, and allowing the resultant to react to thereby obtain the 2,3-bisphosphinopyrazine derivative represented by the following general formula (3). According to the present invention, a method for producing the industrially advantageous 2,3-bisphosphinopyrazine derivative can be provided.
Efficient Preparation of (S)- and (R)- tert -Butylmethylphosphine-Borane: A Novel Entry to Important P-Stereogenic Ligands
Salomó, Ernest,Orgué, Sílvia,Riera, Antoni,Verdaguer, Xavier
, p. 2659 - 2663 (2016/08/11)
A novel one-pot reductive methodology for the synthesis of optically pure tert-butylmethylphosphine-borane is reported. The preparation uses as the starting material tert-butylmethylphosphinous acid-borane, which is available in both enantiomeric forms from cis-1,2-aminoindanol and tert-butyldichlorophosphine. The process is based on the reduction of a mixed anhydride, the configurational stability of which has been studied in several solvents and temperatures. Tetrabutylammonium borohydride was the best reducing agent allowing for the development of a practical process. To demonstrate the utility of the new methodology, the product obtained in this manner was used in the preparation of Quinox-P?.
ANTI-CANCER AGENT
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Page/Page column 6, (2012/10/08)
The anti-cancer agent of the present invention contains at least one kind of phosphine transition metal complex selected from a group of compounds represented by the following Formulae (1a) to (1d). According to this anti-cancer agent, an anti-cancer agent is provided which has a higher anti-cancer activity and lower toxicity compared to anti-cancer agents in the related art. In Formulae (1a), (1b), (1c), and (1d), R1 and R2 represent a linear or branched alkyl group, and R4 has a higher priority than R2 as ranked according to RS notation. R3 and R4 represent a hydrogen atom or a linear or branched alkyl group. M represents an atom of a transition metal selected from a group consisting of gold, copper, and silver. X? represents an anion.
