-iPr-PHOX.svg) | |
| Names | |
|---|---|
| Preferred IUPAC name (4S)-2-[2-(Diphenylphosphanyl)phenyl]-4-(propan-2-yl)-4,5-dihydro-1,3-oxazole | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
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| Properties | |
| C24H24NOP | |
| Molar mass | 373.436 g·mol−1 |
| Appearance | White solid |
| Melting point | 85 to 90 °C (185 to 194 °F; 358 to 363 K) |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
(S)-iPr-PHOX, or (S)-2-[2-(diphenylphosphino)phenyl]-4-isopropyl-4,5-dihydrooxazole, is achiral,bidentate,ligand derived from the amino alcoholvalinol. It is part of a broader class ofphosphinooxazolines ligands and has found application inasymmetric catalysis.
(S)-iPr-PHOX is prepared using the amino alcohol valinol, which is derived fromvaline. Thephosphine moiety may be introduced first, by a reaction between 2-bromobenzonitrile andchlorodiphenylphosphine; the oxazoline ring is then formed in aWitte Seeliger reaction. This yields an air stable zinc complex which must be treated withbipyridine in order to obtain the free ligand. Synthesis is performed under argon or nitrogen to avoid contact with air, however the final product is not air sensitive.
Iridium complexes incorporating (S)-iPr-PHOX have been used forasymmetric hydrogenation.[1]
