DIPAMP

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DIPAMP
DIPAMP.png
DIPAMP-from-xtal-2004-Mercury-3D-balls.png
Names
IUPAC name
Ethane-1,2-diylbis[(2-methoxyphenyl)phenylphosphane]
Identifiers
55739-58-7 (R,R) YesY
97858-62-3 (S,S)
ChemSpider 9594634 YesY
Jmol-3D images Image
Image
PubChem 11419748
Properties
C28H28O2P2
Molar mass 458.47 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY verify (what isYesY/N?)
Infobox references

DIPAMP is an organophosphorus compound that is used as a ligand in homogeneous catalysis. It is a white solid that dissolves in organic solvents. Work on this compound by W. S. Knowles was recognized with the Nobel Prize in Chemistry.[1] DIPAMP was the basis for of the first industrial scale asymmetric hydrogenation, the synthesis of the drug L-DOPA.[2]

L-DOPA synthesis2.png

DIPAMP is a chelating diphosphine. Each phosphorus centre, which is pyramidal, bears three different substituents - anisyl, phenyl, and the ethylene group. It therefore exists as the enantiomeric (R,R) and (S,S) pair, as well as the achiral meso isomer.

DIPAMP was originally prepared by an oxidative coupling reaction, starting from anisyl(phenyl)(methyl)phosphine.

References[edit]

  1. ^ Knowles, William S. (2002). "Asymmetric Hydrogenations (Nobel Lecture) Copyright© The Nobel Foundation 2002. We thank the Nobel Foundation, Stockholm, for permission to print this lecture.". Angewandte Chemie International Edition 41 (12): 1998. doi:10.1002/1521-3773(20020617)41:12<1998::AID-ANIE1998>3.0.CO;2-8. 
  2. ^ Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. (1977). "Asymmetric hydrogenation. Rhodium chiral bisphosphine catalyst". Journal of the American Chemical Society 99 (18): 5946–5952. doi:10.1021/ja00460a018.