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DIPAMP

Chemical compound

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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. DIPAMP was the basis for one of the first industrial scale asymmetric hydrogenation, the synthesis of the drug L-DOPA.

DIPAMP is a C2-symmetric diphosphine. Each phosphorus centre, which is pyramidal, bears three different substituents - anisyl, phenyl, and the ethylene group. The ligand 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, starting from anisyl(phenyl)(methyl)phosphine.

Synthesis of L-DOPA via hydrogenation with the C2-symmetric diphosphine DIPAMP.
Synthesis of L-DOPA via hydrogenation with the C2-symmetric diphosphine DIPAMP.
Structure of [Rh(DIPAMP)(cod)]+ by X-ray crystallography.
Structure of [Rh(DIPAMP)(cod)]+ by X-ray crystallography.
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This article is adapted from the Wikipedia article DIPAMP, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.

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