New electron-deficient chiral phosphines: (4R,5R)-1,3-bis(trifluoromethanesulfonyl)perhydro-1,3,2-benzodiazaphosphol-2-yl] substituted amines

Acta Crystallogr C. 2002 Feb;58(Pt 2):o108-11. doi: 10.1107/s0108270101018200. Epub 2002 Jan 23.

Abstract

Three chiral electron-deficient phosphine ligands, [(4R,15R)-,3-bis(trifluoromethanesulfonyl)perhydro-1,3,2-benzodiazaphosphol-2-yl]diethylamine, C(12)H(20)F(6)N(3)O(4)PS(2), (IIIa), [(4R,5R)-1,3-bis(trifluoromethanesulfonyl)perhydro-1,3,2-benzodiazaphosphol-2-yl]dimethylamine, C(10)H(16)F(6)N(3)O(4)PS(2), (IIIb), and bis[(4R,5R)-1,3-bis(trifluoromethanesulfonyl)perhydro-1,3,2-benzodiazaphosphol-2-yl]methylamine, (IV), as the chloroform solvate, C(17)H(23)F(12)N(5)O(8)P(2)S(4).0.98CHCl(3), have been prepared from (1R,2R)-N,N'-bis(trifluoromethanesulfonyl)-1,2-cyclohexanediamine and diethyl phosphoramidous dichloride, dimethyl phosphoramidous dichloride or methyl imidodiphosphorus tetrachloride. The pi-acceptor abilities of these new types of ligands have been evaluated by X-ray determination of the P-N bond lengths; it has been found that the most promising ligand is the bis(phosphine) (IV).