| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348875 | Tetrahedron: Asymmetry | 2010 | 11 Pages |
A series of novel quarternary ammonium salt-modified chiral ferrocenylphosphine-imine ligands have been synthesized and the molecular structure of BIT5 has been determined by single-crystal X-ray diffraction. The applicability of these ligands in asymmetric C∗–C and C∗–N bond formation was demonstrated. High enantioselectivity was obtained in the Pd-catalyzed asymmetric substitution of 1,3-diphenyl-2-propenyl acetate, with dimethyl malonate (up to 94.6% ee) and benzylamine (up to 92.6% ee).
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4-[(E)-[[(1R)-1-[(2S)-2-(Diphenylphosphino)ferrocenyl]ethyl]imino]methyl]-N,N,N-trimethyl-benzenaminium, iodideC34H36FeIN2P[α]D = −354.3 (c 0.6, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,Sp)
4-[(E)-[[(1R)-1-[(2S)-2-(Diphenylphosphino)ferrocenyl]ethyl]imino]methyl]-N,N,N-trimethyl-benzenaminium, bromideC34H36BrFeN2P[α]D = −369.0 (c 0.6, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,Sp)
4-[(E)-[[(1R)-1-[(2S)-2-(Diphenylphosphino)ferrocenyl]ethyl]imino]methyl]-N,N,N-trimethyl-benzenaminium, trifluoromethane sulfonateC34H36F3FeN2O3PS[α]D = −353.9 (c 0.6, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,Sp)
4-[(E)-[[(1R)-1-[(2S)-2-(Diphenylphosphino)ferrocenyl]ethyl]imino]methyl]-N,N,N-trimethyl-benzenaminium, p-toluenesulfonateC41H43F3FeN2O3PS[α]D = −368.3 (c 0.6, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,Sp)
4-[(E)-[[(1R)-1-[(2S)-2-(Diphenylphosphino)ferrocenyl]ethyl]imino]methyl]-N,N,N-trimethyl-benzenaminium, acetateC36H39FeN2O2P[α]D = −345.0 (c 0.6, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,Sp)
4-[(E)-[[(1R)-1-[(2S)-2-(Diphenylphosphino)ferrocenyl]ethyl]imino]methyl]-N,N,N-trimethyl-benzenaminium, nitrateC34H36FeN3O3P[α]D = −355.7 (c 0.6, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,Sp)
4-[(E)-[[(1R)-1-[(2S)-2-(Diphenylphosphino)ferrocenyl]ethyl]imino]methyl]-N,N,N-trimethyl-benzenaminium, hexafluorophosphateC34H36F6FeN2P2[α]D = −364.75 (c 0.6, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,Sp)
3-[(E)-[[(1R)-1-[(2S)-2-(Diphenylphosphino)ferrocenyl]ethyl]imino]methyl]-N,N,N-trimethyl-benzenaminium, iodideC34H36FeIN2P[α]D = −347.2 (c 0.6, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,Sp)
2-[(E)-[[(1R)-1-[(2S)-2-(Diphenylphosphino)ferrocenyl]ethyl]imino]methyl]-N,N,N-trimethyl-benzenaminium, iodideC34H36FeIN2P[α]D = −339.85 (c 0.6, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,Sp)
4-[(E)-[[(1R)-1-[(2S)-2-(Diphenylphosphino)ferrocenyl]ethyl]imino]methyl]-N,N,N-trimethyl-benzenemethanaminium, iodideC35H38FeIN2P[α]D = −352.3 (c 0.6, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,Sp)
N-[4-[(E)-[[(1R)-1-[(2S)-2-(Diphenylphosphino)ferrocenyl]ethyl]imino]methyl]]-N,N-dimethyl-benzenemethanaminium, bromideC40H40BrFeN2P[α]D = −376.25 (c 0.6, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,Sp)
(S,E)-Dimethyl 2-(1,3-diphenylallyl)malonateC20H20O4[α]D = −17.0 (c 1.5, ethanol, 94.6% ee)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S,E)-Diethyl 2-(1,3-diphenylallyl)malonateC22H24O4[α]D = −16.9 (c 1.0, CHCl3, 94.0% ee)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S,E)-Diethyl 2-(1,3-diphenylallyl)-2-methylmalonateC23H26O4[α]D = −29.9 (c 0.6, CHCl3, 91.0% ee)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S,E)-Dibenzyl 2-(1,3-diphenylallyl)malonateC32H28O4[α]D = −7.9 (c 1.6, CHCl3, 91.6% ee)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(R,E)-N-Benzyl-1,3-diphenylprop-2-en-1-amineC22H21N[α]D = −18.8 (c 0.15, CHCl3, 92.6% ee)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(R,E)-N-(1,3-Diphenylallyl)benzohydrazideC22H20N2O[α]D = −35.7 (c 0.73, CHCl3, 91.4% ee)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(R,E)-N-(1,3-Diphenylallyl)phthalimideC23H17NO2[α]D = −19.7 (c 1.7, CHCl3, 89.9% ee)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(R,E)-1-(1,3-Diphenylallyl)pyrrolidineC19H21N[α]D = −2.4 (c 1.0, CHCl3, 40.2% ee)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(R,E)-4-(1,3-Diphenylallyl)morpholineC19H21NO[α]D = −3.8 (c 0.34, CHCl3, 33.5% ee)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
