Basic information Reactions Safety Supplier Related

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

Basic information Reactions Safety Supplier Related

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

Product Name:
(1R,1'R,2S,2'S)-DUANPHOS
Synonyms:
  • (1R,1'R,2S,2'S)-2,2'-Bis(1,1-dimethylethyl)-2,2',3,3'-tetrahydro-1,1'-bi-1H-isophosphindole,99%e.e.
  • (1R,1'R,2S,2'S)- 2,2'-bis(1,1-diMethylethyl)-2,2',3,3'-tetrahydro-1,1'-Bi-1H-isophosphindole
  • (1R,1'R,2S,2'S)-(+)-2,2'-Di-t-butyl-2,3,2',3'-tetrahydro-1,1'-bi-1H-isophosphindole (R,R,S,S)-DUANPHOS
  • RcSp-DuanPhos
  • 1,1'-Bi-1H-isophosphindole, 2,2'-bis(1,1-dimethylethyl)-2,2',3,3'-tetrahydro-, (1R,1'R,2S,2'S)-
  • (1R,1'R,2S,2'S)-2,2'-di-tert-butyl-2,2',3,3'-tetrahydro-1H,1'H-1,1'-biisophosphindole
  • (1R,1'R,2S,2'S)-(+)-2,2'-Di-t-butyl-2,3,2',3'-tetrahydro-1,1'-bi-1H-isophosphindole
  • (1R,1'R,2S,2'S)-DUANPHOS
CAS:
528814-26-8
MF:
C24H32P2
MW:
382.46
Mol File:
528814-26-8.mol
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(1R,1'R,2S,2'S)-DUANPHOS Chemical Properties

Melting point:
214-246 °C
alpha 
+19.5
Boiling point:
474.5±45.0 °C(Predicted)
form 
crystal
color 
white
optical activity
[α]20/D +18°, c = 1 in chloroform
Sensitive 
air sensitive
CAS DataBase Reference
528814-26-8
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Safety Information

WGK Germany 
3
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(1R,1'R,2S,2'S)-DUANPHOS Usage And Synthesis

Reactions

  1. As a highly electron-donating and conformationally rigid ligand, the rhodium complex of DuanPhos has exhibited remarkably high enantioselectivities and reactivities for the hydrogenation of a variety of functionalized olefins.
  2. Rhodium/DUANPHOS catalyst used in the synthesis of 2-trifluoromethyl lactic acid by asymmetric hydroformylation.

Uses

Chiral Quest Phosphine Ligands for Asymmetric Hydrogenation

Catalytic ligand used for:

  • Stereoselective synthesis of cyano-substituted dihydropyrroles by annulation of cyanoallenes
  • Rhodium-catalyzed intermolecular enantioselective hydroacylation of alkynes to give alpha- and beta-substituted unsaturated ketones by kinetic resolution
  • Stereoselective preparation of β-amino nitriles via rhodium-catalyzed asymmetric hydrogenation of amino acrylonitriles
  • Stereoselective preparation of anti-1,3-amino alcohols via rhodium-catalyzed asymmetric hydrogenation of β-ketoenamide intermediates
  • Stereoselective preparation of acetylaminoindane via rhodium-catalyzed asymmetric hydrogenation of acetylaminoindene

General Description

(1R,1′R,2S,2′S)-DuanPhos is an electron-rich chiral phosphine ligand mainly for transition metal catalyzed asymmetric hydrogenation.

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