SEGPHOS

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SEGPHOS
Skeletal formula of SEGPHOS
Space-filling model of the SEGPHOS molecule
Names
IUPAC name
4,4'-Bi-1,3-benzodioxole-5,5'-diylbis(diphenylphosphane)
Other names
SEGPHOS
5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole
Identifiers
244261-66-3 (R) YesY
210169-54-3 (S) N
3D model (Jmol) (RS): Interactive image
ChemSpider 9192694 (RS) N
PubChem 11017510 (RS)
Properties
C38H28O4P2
Molar mass 610.57 g/mol
Appearance colorless solid
organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

SEGPHOS is a chiral ligand developed by Takasago that is used in asymmetric synthesis.[1] It was developed after BINAP and was investigated since it has a narrower dihedral angle between the aromatic faces. This was predicted and then confirmed to increase the enantioselectivity and activity of metal complexes of SEGPHOS.

In addition to the parent ligand bearing phenyl groups on the phosphorus atoms, the bulkier derivatives DM-SEGPHOS and DTBM-SEGPHOS are also commercially available.[2] In DM-SEGPHOS and DTBM-SEGPHOS, the phenyl groups of SEGPHOS are replaced by 3,5-dimethylphenyl and 3,5-di-t-butyl-4-methoxyphenyl groups, respectively.

Segphos family.png

References[edit]

  1. ^ Shimizu, H., Nagasaki, I., Matsumura, K., Sayo, N., Saito, T. (2007). "Developments in Asymmetric Hydrogenation from an Industrial Perspective". Acc. Chem. Res. 40 (12): 1385–1393. doi:10.1021/ar700101x. PMID 17685581. 
  2. ^ "SEGPHOS". www.strem.com. Retrieved 2016-08-10.