Tetrahydrofuran → (1-Methyl-2-nitroethyl)benzene

Participants

Reaction Steps

In a 10 mL Schlenk-flask, 6.8 mg of cuprous tert-butoxide and 37.3 mg of (S)-p-tol-BINAP were dissolved in 5 ml of toluene. After stirring for 30 minutes at room temperature to give an asymmetric copper complex. One hundred microliters (100 μL) of this solution (containing 1 μmol of the asymmetric copper complex) were mixed with 4.9 ml of toluene, and 90 μL (1.5 mmol) of poly(methylhydrosiloxane) (15-40 mPas (20° C.), d=1.004 g/mL, nD20=1.398, produced by Fluka) and 221 mg (1.2 mmol) of diphenylsilane were added thereto. After stirring for 5 minutes, 1 mmol of (E)-1-nitro-2-phenyl-1-propene was added, and the mixture was further stirred for 24 hours at room temperature. Four milliliters (4 mL) of a tetrahydrofuran solution of tetrabutylammonium fluoride (1 mol/L) were added to the reaction mixture and stirring was continued for 3 hours. Water was added and the mixture was extracted with diethyl ether (30 mL×2). After drying over sodium sulfate, the solvent was evaporated. The residue was purified by flash chromatography (silica gel, hexane/ethyl acetate) to provide optically active 1-nitro-2-phenylpropane.

Provenance & Evidence