Tetrafluoroborate → HCID 21713174, compound

Reaction equation

[CH2:1](/[C:4](=[CH:8]\[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10])/[C:5]([OH:7])=[O:6])[CH2:2][CH3:3].F[B-](F)(F)F.[H][H]>CO>[C:12]1([S:9]([CH2:8][CH:4]([CH2:1][CH2:2][CH3:3])[C:5]([OH:7])=[O:6])(=[O:11])=[O:10])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Procedure

(E)-2-Propyl-3-phenylsulfonylacrylic acid (0.3 g, 1.18 mmol) was dissolved in degassed methanol (15 ml) and [(S,S)-EtDuPHOS Rh (COD)]BF4 (8 mg, 1.18×10−2 mmol) was added under a stream of nitrogen. This solution was injected into the pressure vessel under nitrogen, and then the bomb was charged with hydrogen. The mixture was hydrogenated at 2070 kPa (300 psi) for 3 hour at room temperature. The methanol was removed under reduced pressure to give the title compound (0.31 g, 100% yield). E.e. was determined by chiral HPLC to be 92% e.e. [Chiropak AD; 5% ethanol-95% heptane; 1 ml/min; 254 nm; major enantiomer Rf 18.46 min., minor enantiomer Rf 15.22 min.]