2063. (S,S)-Chiraphos

Nomenclature

CAS number: 64896-28-2
[(1S,2S)-1,2-Dimethyl-1,2-ethanediyl]bis[diphenylphosphine]; (2S,3S)-(-)-bis(diphenylphosphino)butane.
C28H28P2; mol wt 426.47.
C 78.86%, H 6.62%, P 14.53%.

Description and references

Chiral, bidentate phosphine ligand in asymmetric catalysis. Prepn: M. D. Fryzuk, B. Bosnich, J. Am. Chem. Soc. 99, 6262 (1977); J. F. G. Jansen, B. L. Feringa, Tetrahedron: Asymmetry 1, 719 (1990); S. H. Bergens et al., Inorg. Synth. 31, 131 (1997). 1H and 31P NMR of platinum complexes: N. C. Payne, D. W. Stephan, J. Organomet. Chem. 221, 203 (1981). Synthetic applications: C. Moinet, J.-C. Fiaud, Tetrahedron Lett. 36, 2051 (1995); H. Frauenrath et al., Tetrahedron: Asymmetry 9, 1103 (1998); K. Akiyama et al., Adv. Synth. Catal. 347, 1569 (2005).

Chemical structure

Properties

Large, colorless plates from absolute ethanol, mp 108-109°. [α]D27 -211° (c = 1.5 in CHCl3). Sol in acetone, THF, dichloromethane, chloroform, diethyl ether, toluene, hot ethanol. Insol in hexanes, methanol, cold ethanol.

Use

Ligand for palladium-catalyzed carbon-carbon bond formation.