DuPHOS

Title: DuPHOS
Literature References: Series of chiral bis(phospholane) compounds with C2 symmetry used as rhodium complexes for catalysis. Prepn: M. J. Burk, J. Am. Chem. Soc. 113, 8518 (1991); and configuration: idem et al., ibid. 115, 10125 (1993). Use in asymmetric synthesis of warfarin: A. Robinson et al, Tetrahedron Lett. 37, 8321 (1996); hydrogena-tions of b-(acylamino)acrylates: G. Zhu et al., J. Org. Chem. 64, 6907 (1999).
Derivative Type: (R,R)-Me-DuPHOS
CAS Registry Number: 147253-67-6
CAS Name: [2R-[1(2¢R*,5¢R*),2a,5b]]-1,1¢-(1,2-Phenylene)bis[2,5-dimethylphospholane]
Molecular Formula: C18H28P2
Molecular Weight: 306.36
Percent Composition: C 70.57%, H 9.21%, P 20.22%
Derivative Type: (S,S)-Me-DuPHOS
CAS Registry Number: 136735-95-0
Additional Names: (S,S)-1,2-Bis(2,5-dimethylphospholano)benzene
Molecular Formula: C18H28P2
Molecular Weight: 306.36
Percent Composition: C 70.57%, H 9.21%, P 20.22%
Properties: Colorless crystals from methanol, mp 79-81°. [a]D25 +476± 5° (c = 1 in hexane).
Melting point: mp 79-81°
Optical Rotation: [a]D25 +476± 5° (c = 1 in hexane)
Derivative Type: (R,R)-Et-DuPHOS
CAS Registry Number: 136705-64-1
CAS Name: (2R,2¢R,5R,5¢R)-1,1¢-(1,2-Phenylene)bis[2,5-diethylphospholane]
Molecular Formula: C22H36P2
Molecular Weight: 362.47
Percent Composition: C 72.90%, H 10.01%, P 17.09%
Properties: Colorless oil. [a]D25 -265° (c = 1 in hexane). bp0.045 138-145°.
Boiling point: bp0.045 138-145°
Optical Rotation: [a]D25 -265° (c = 1 in hexane)
Use: Catalyst for asymmetric hydrogenations.
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