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

In a 10 mL Schlenk-flask, 6.8 mg of copper (I) tert-butoxide and 32.7 mg (55 μmol) 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. This solution to the amount containing 1 μmol of the asymmetric copper complex were mixed with 4.9 ml of toluene, and 6 μL (0.1 mmol) of poly(methylhydrosiloxane) (15-40 mPas (20° C.), d=1.004 g/mL, nD20=1.398, produced by Fluka) were added thereto. Further, 185 μL of (1.5 mmol) of phenylsilane and 27 μL (1.5 mmol) of water were added. 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.

1. customto give an asymmetric copper complex
2. additionThis solution to the amount containing 1 μmol of the asymmetric copper complex
3. customnD20=1.398, produced by Fluka)
4. additionwere added
5. stirringAfter stirring for 5 minutes
6. stirringthe mixture was further stirred for 24 hours at room temperature
7. stirringstirring
8. waitwas continued for 3 hours
9. extractionthe mixture was extracted with diethyl ether (30 mL×2)
10. dry with materialAfter drying over sodium sulfate
11. customthe solvent was evaporated
12. customThe residue was purified by flash chromatography (silica gel, hexane/ethyl acetate)

ORD record

ord-d08fd2529e994c049be6c329e95ae7d4

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790900B2