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657697

Sigma-Aldrich

(1R,1′R,2S,2′S)-DuanPhos

Synonym(s):

(1R,1′R,2S,2′S)-2,2′-Di-tert-butyl-2,3,2′,3′-tetrahydro-1H,1′H-(1,1′)biisophosphindolyl

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About This Item

Empirical Formula (Hill Notation):
C24H32P2
CAS Number:
528814-26-8
Molecular Weight:
382.46
UNSPSC Code:
12352005
PubChem Substance ID:
24884305
NACRES:
NA.22

optical activity

[α]20/D +18°, c = 1 in chloroform

Quality Level

100

mp

214-246 °C

functional group

phosphine

SMILES string

CC(C)(C)P1Cc2ccccc2C1C3P(Cc4ccccc34)C(C)(C)C

InChI

1S/C24H32P2/c1-23(2,3)25-15-17-11-7-9-13-19(17)21(25)22-20-14-10-8-12-18(20)16-26(22)24(4,5)6/h7-14,21-22H,15-16H2,1-6H3/t21-,22-,25-,26-/m1/s1

InChI key

HCBRTCFUVLYSKU-SAZLYLDSSA-N

Related Categories

General description

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

Application

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

657697-VAR:
657697-100MG:
657697-500MG:
657697-500MG-PW:
657697-BULK:
657697-100MG-PW:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS0998
MKCQ5623
MKCP6020
MKCM8542
MKCM0918

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Articles

Chiral Quest Phosphine Ligands

Sigma-Aldrich has research quantities of a series of Zhang’s chiral phosphines for catalytic asymmetric hydrogenations.

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