1,1,1,3,3,3-Hexafluoro-2-propanol → Methyl-duphos, (S,S)-

HRID 441108Notes

Reaction equation

HRID 441108 reaction equation
C(O)(C(F)(F)F)C(F)(F)F.[CH3:11][C@H:12]1[P:16]([C:17]2[C:22]([P:23]3[C@H:27]([CH3:28])[CH2:26][CH2:25][C@H:24]3[CH3:29])=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:15]([CH3:30])[CH2:14][CH2:13]1>C(Cl)(Cl)Cl>[CH3:28][C@@H:27]1[P:23]([C:22]2[C:17]([P:16]3[C@@H:12]([CH3:11])[CH2:13][CH2:14][C@@H:15]3[CH3:30])=[CH:18][CH:19]=[CH:20][CH:21]=2)[C@@H:24]([CH3:29])[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanol2×HCID 2734551Methyl-duphos, (R,R)-

Product 1

HCID 2734553Methyl-duphos, (S,S)-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Molar optical rotation: [Φ]D25 =-64.0° (c=3.26 mg/ml, CHCl3), [Φ]D25 =+7° (c=7.27 mg/ml (CF3)2CHOH). (R,R)-Me-DUPHOS Ligand: Molar optical rotation: [Φ]D25 =+65.0° (c= 3.26 mg/ml, CHCl3), [Φ]D25 =-7° (c=7.27 mg/ml, (CF3)2CHOH).

Sources & evidence

ORD record
ord-d34157fb000e4541a5a85b24468af4a3
Source dataset
uspto-grants-1996_05
Patent number
US05521281

Reaction notes

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