135139-00-3 Usage
Description
(S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl is a chiral biaryl bisphosphine ligand that plays a crucial role in various catalytic applications, particularly in the field of organic synthesis. It is known for its ability to induce high levels of enantioselectivity and regioselectivity in a range of chemical reactions, making it a valuable tool for the synthesis of complex molecules with precise stereochemistry.
Uses
Used in Asymmetric Hydrogenation:
(S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl is used as a catalyst in the asymmetric hydrogenation of benzophenone. It facilitates the selective reduction of the carbonyl group, leading to the formation of chiral alcohols with high enantiomeric excess.
Used in Regioand Stereoselective Preparation of Axially Chiral Arylnaphthalene Derivatives:
In the application industry of organic synthesis, (S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl is used as a ligand for the rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives. This reaction results in the formation of axially chiral arylnaphthalene derivatives with high regioand stereoselectivity.
Used in Regiodivergent Rhodium-Catalyzed [(2+2)+2] Carbocyclization:
(S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl is employed as a ligand in the regiodivergent rhodium-catalyzed [(2+2)+2] carbocyclization of 1,6-enynes with Me propiolates. This reaction allows for the selective formation of different cyclization products, depending on the reaction conditions and the choice of ligand.
Used in Ligand Controlled Regioselective and Stereoselective Desymmetrizing Rhodium-Catalyzed Allylic Arylation:
In the field of organic synthesis, (S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl is used as a ligand for the desymmetrizing rhodium-catalyzed allylic arylation of meso cyclopentene dicarbonates with arylboronic acids. This reaction leads to the formation of regioisomeric arylcyclopentenols with high regioand stereoselectivity.
Used in Platinum(II) Complex-Catalyzed Enantioselective Aldol Reaction:
(S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl is utilized as a ligand in the platinum(II) complex-catalyzed enantioselective aldol reaction with ketene silyl acetals in DMF at room temperature. This reaction provides a highly enantioselective route to chiral aldols, which are important building blocks in organic synthesis.
Used in Stereoselective Preparation of Chiral N,O-Biaryls:
In the application industry of organic synthesis, (S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl is used as a ligand for the Rh-catalyzed [2+2+2] cycloaddition of conjugate ynamides with diynes. This reaction results in the formation of chiral N,O-biaryls with high stereoselectivity, which are valuable intermediates in the synthesis of various biologically active compounds.
Reaction
Ligand used in copper-catalyzed asymmetric Mannich-type reactions of N-acylimino esters.
Ligand used in the enantioselective fluorination of oxindoles.
Ligand used in [2+2+2] cycloaddition of tetraynes and hexaynes.
Ligand used in the asymmetric reduction of ketone via ruthenium-catalyzed transfer hydrogenation.
Asymmetric hydroboration of unsaturated imines.
Check Digit Verification of cas no
The CAS Registry Mumber 135139-00-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,5,1,3 and 9 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 135139-00:
(8*1)+(7*3)+(6*5)+(5*1)+(4*3)+(3*9)+(2*0)+(1*0)=103
103 % 10 = 3
So 135139-00-3 is a valid CAS Registry Number.
InChI:InChI=1/C52H48P2/c1-33-21-34(2)26-43(25-33)53(44-27-35(3)22-36(4)28-44)49-19-17-41-13-9-11-15-47(41)51(49)52-48-16-12-10-14-42(48)18-20-50(52)54(45-29-37(5)23-38(6)30-45)46-31-39(7)24-40(8)32-46/h9-32H,1-8H3
135139-00-3Relevant articles and documents
Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases
Ryoo, Jae Jeong,Yu, Jeong Jae
, (2022/01/20)
Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative
A 2,2 the [...] -bis [(3,5- xylyl ) phosphorus] dinaphthalene method for the preparation of
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Paragraph 0028; 0042; 0043, (2017/02/28)
The invention relates to the field of organic synthesis, and in particular relates to a method for preparing 2, 2'-bis [(3, 5-xylyl) phosphorus) dinaphthalene. The method comprises the following steps: preparing N-methyl piperazine phosphorus dichloride h
Improved syntheses of phosphine ligands by direct coupling of diarylbromophosphine with organometallic reagents
Liu, Lei,Wu, Hai-Chen,Yu, Jin-Quan
scheme or table, p. 10828 - 10831 (2011/11/04)
Br versus Cl: It is found that the use of diarylbromophosphines instead of diarylchlorophosphines is crucial for their direct coupling with binaphthylmagnesium bromide or BINOL triflate. This finding has led to an improved preparation of both electron-deficient BINAP-type phosphine ligands and several important Buchwald's ligands. Copyright
