HCID 10953851, compound → (3-Nitroprop-1-en-2-yl)benzene

Participants

Reaction Steps

In a 10 mL Schlenk-flask, 8 mg of copper (I) chloride and 8 mg of sodium tert-butoxide and 110 mg of (S)-p-tol-BINAP were dissolved in 6 ml of toluene. After stirring for 15 minutes at room temperature to give an asymmetric copper complex. Into this solution, 360 μL (6.0 mmol) of poly(methylhydrosiloxane) (15-40 mPas (20° C.), d=1.004 g/mL, nD20=1.398, produced by Fluka) and 32 mg of water were added. After stirring for 5 minutes, 1.5 mmol of (E)-1-nitro-2-phenyl-1-propene were added, and the mixture was further stirred for 22 hours at room temperature. 1H-NMR analysis showed that the objective optically active 1-nitro-2-phenylpropane was provided in 50% yield. A by-product, 1-nitro-2-phenyl-2-propene was provided in 4% yield.

Provenance & Evidence