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682869

Sigma-Aldrich

(11bS,11′bS)-4,4′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin

Synonym(s):

S,S-Reetz X-Diphosphonite

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About This Item

Empirical Formula (Hill Notation):
C55H36O5P2
CAS Number:
349114-57-4
Molecular Weight:
838.82
MDL number:
MFCD09842740
UNSPSC Code:
12352005
PubChem Substance ID:
329760513
NACRES:
NA.22

form

solid

optical activity

[α]22/D -245°, c = 1 in chloroform

mp

195-207 °C (dec.)

SMILES string

CC1(C)c2cccc(P3Oc4ccc5ccccc5c4-c6c(O3)ccc7ccccc67)c2Oc8c(cccc18)P9Oc%10ccc%11ccccc%11c%10-c%12c(O9)ccc%13ccccc%12%13

InChI

1S/C55H36O5P2/c1-55(2)41-21-11-23-47(61-57-43-29-25-33-13-3-7-17-37(33)49(43)50-38-18-8-4-14-34(38)26-30-44(50)58-61)53(41)56-54-42(55)22-12-24-48(54)62-59-45-31-27-35-15-5-9-19-39(35)51(45)52-40-20-10-6-16-36(40)28-32-46(52)60-62/h3-32H,1-2H3

InChI key

DXZANFKSPAISOB-UHFFFAOYSA-N

Application

  • Catalyst for asymmetric hydrogenation of quinolines catalyzed by iridium complexes of BINOL-derived diphosphonites
  • Ligand in asymmetric Ni-catalyzed hydrocyanation of styrene and other vinylarenes
This diphosphonite ligand has been successfully employed in Noyori-type asymmetric transfer hydrogenation of prochiral ketones.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Manfred T Reetz et al.
Journal of the American Chemical Society, 128(4), 1044-1045 (2006-01-26)
A BINOL-derived diphosphonite having a xanthene backbone is an excellent bidentate ligand in Ru-catalyzed 2-propanol-based transfer hydrogenation of aryl/alkyl and alkyl/alkyl ketones (ee = 76-99%). Even notoriously difficult ketones such as isopropyl methyl ketone are reduced with extraordinarily high enantioselectivity

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