(1R,1'R,2S,2'S)-DUANPHOS

Base Information

• Chemical Name: (1R,1'R,2S,2'S)-DUANPHOS
• CAS No.: 528814-26-8
• Molecular Formula: C24H32P2
• Molecular Weight: 382.46
• Mol file: 528814-26-8.mol

Synonyms:(1R,1'R,2S,2'S)-DuanPhos;

Chemical Property of (1R,1'R,2S,2'S)-DUANPHOS

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 214-246 °C
• Boiling Point: 474.52°C at 760 mmHg
• Flash Point: 255.314°C
• PSA: 27.18000
• LogP: 8.05700
• Sensitive.: air sensitive

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1R,1'R,2S,2'S)-(+)-2,2'-Di-t-butyl-2,3,2',3'-tetrahydro-1,1'-bi-1H-isophosphindole, min. 98% (R,R,S,S)-DUANPHOS ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Chiral Quest Phosphine Ligands for Asymmetric HydrogenationCatalytic ligand used for:Stereoselective synthesis of cyano-substituted dihydropyrroles by annulation of cyanoallenesRhodium-catalyzed intermolecular enantioselective hydroacylation of alkynes to give alpha- and beta-substituted unsaturated ketones by kinetic resolutionStereoselective preparation of β-amino nitriles via rhodium-catalyzed asymmetric hydrogenation of amino acrylonitrilesStereoselective preparation of anti-1,3-amino alcohols via rhodium-catalyzed asymmetric hydrogenation of β-ketoenamide intermediatesStereoselective preparation of acetylaminoindane via rhodium-catalyzed asymmetric hydrogenation of acetylaminoindene

Technology Process of (1R,1'R,2S,2'S)-DUANPHOS

There total 12 articles about (1R,1'R,2S,2'S)-DUANPHOS which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

(+)-2,2'-di-tert-butyl-1,3,1',3'-tetrahydro-[1,1']biisophosphindolyl 2,2'-dioxide (795289-53-1) → (Rc,Sp)-DuanPhos (528814-26-8)

Guidance literature:

With TEA; trichlorosilane; In toluene; at 70 ℃; for 16h;

DOI:10.1002/ejoc.200400690

Reference yield:

(-)-2,2'-di-tert-butyl-1,3,1',3'-tetrahydro-[1,1']biisophosphindolyl 2,2'-dioxide (795289-52-0) → (Sc,Rp)-DuanPhos (528814-26-8)

Guidance literature:

With TEA; trichlorosilane; In toluene; at 70 ℃; for 16h;

DOI:10.1002/ejoc.200400690

Reference yield:

1,5-dihydro-benzo[e][1,3,2]dioxathiepine (795289-50-8) → (Sc,Rp)-DuanPhos (528814-26-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaIO₄ / RuCl₃*xH₂O / acetonitrile; CHCl₃; H₂O / 1 h / 0 °C

2.1: LDA / tetrahydrofuran / -78 - 20 °C

2.2: CuCl₂ / tetrahydrofuran / -78 - 20 °C

3.1: (D)-dibenzoyl tartaric acid ((D)-DBT*H₂O) / methanol / 4 h / Heating

4.1: HSiCl₃; TEA / toluene / 16 h / 70 °C

With sodium periodate; D-(+)-O,O'-dibenzoyltartaric acid; TEA; trichlorosilane; lithium diisopropyl amide; ruthenium trichloride; In tetrahydrofuran; methanol; chloroform; water; toluene; acetonitrile;

DOI:10.1002/ejoc.200400690

upstream raw materials:

(-)-2,2'-di-tert-butyl-1,3,1',3'-tetrahydro-[1,1']biisophosphindolyl 2,2'-dioxide

1,5-dihydro-benzo[e][1,3,2]dioxathiepine

phthalyl alcohol

2-tert-butyl-1,3-dihydro-isophosphindole 2-oxide

Refernces