DIOP
200px | |
Names | |
---|---|
IUPAC name
O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane
|
|
Other names
(−)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane
(−)-1,4-Bis(diphenylphosphino)-1,4-dideoxy-2,3-O-isopropylidene-L-threitol |
|
Identifiers | |
32305-98-9 (–) 37002-48-5 (+) |
|
ChemSpider | 350240 (–) |
Jmol 3D model | (–): Interactive image |
PubChem | 395120 (–) |
|
|
|
|
Properties | |
C31H32O2P2 | |
Molar mass | 498.54 g·mol−1 |
Appearance | White solid |
Melting point | 86 to 89 °C (187 to 192 °F; 359 to 362 K) |
Insoluble | |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
|
Infobox references | |
DIOP (2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane) is an organophosphorus compound that is used as a chiral ligand in asymmetric catalysis. It is a white solid that is soluble in organic solvents.
Synthesis
DIOP is prepared from the acetonide of d,l-tartaric acid, which is reduced prior to attachment of the PPh2 substituents.
Use
The DIOP ligand binds to metals via conformationally flexible seven-membered C5P2M chelate ring.[1][2]
DIOP is a historically important in the development of asymmetric catalysis, an atom-economical method for the preparation of chiral compounds. Described in 1971, it was the first example of a C2-symmetric disphosphine,[3] Its complexes have been applied to the reduction of prochiral olefins, ketons, and imines. Knowles et al. independently reported the related C2-symmetric diphosphine DIPAMP.[1]
Since the discovery of DIOP, many analogues of DIOP have been introduced. These DIOP derivatives include MOD-DIOP, Cy-DIOP, DIPAMP, and DBP-DIOP. Out of many derivatives, DBP-DIOP exhibits good regio- and enantioselectivity in the hydroformylation of butenes and styrene. DIOP was the first chiral ligand used in the platinum-tin-catalyzed hydroformylation. The reactivity, chemo – and the enantioselectivity of DIOP is influenced by CO and H2 pressure and polarity of the solvents. The best results in asymmetric hydroformylation are achieved in solvents with medium polarity: benzene and toluene.[2]
References
- Pages with broken file links
- Chemical articles with multiple CAS Registry Numbers
- Articles without EBI source
- Articles without KEGG source
- Articles without UNII source
- Pages using collapsible list with both background and text-align in titlestyle
- Articles containing unverified chemical infoboxes
- Chelating agents
- Bisphosphanes