Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [N+:1](/[CH:4]=[C:5](/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)\[CH3:6])([O-:3])=[O:2].[N+](CC(C1C=CC=CC=1)C)([O-])=O>>[N+:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[CH2:6])([O-:3])=[O:2]
Reactant: C/C(=C\[N+](=O)[O-])c1ccccc1
Agent: CC(C[N+](=O)[O-])c1ccccc1
Product: C=C(C[N+](=O)[O-])c1ccccc1
Reaction time: 0.08 h
Yield: 4 %

Procedure:
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.
Reaction SMILES: [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][O:15]C(=O)C)[C@H:10]([O:19][CH2:20][O:21][CH3:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][OH:15])[C@H:10]([O:19][CH2:20][O:21][CH3:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
Reactant: COCO[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]1COC(C)=O
Agent: [Na+]
Agent: [OH-]
Solvent: C1CCOC1
Solvent: CO
Product: COCO[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]1CO
Yield: 88.4 %

Procedure:
A solution of (±)-cis-4-acetoxymethyl-3-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester (41.9 mmol, 13.3 g) in THF (100 mL), MeOH (25 mL), and 2 N NaOH (25 mL) was stirred for 3 hours at room temperature. The THF and MeOH were removed under reduced pressure. The crude product was extracted from the water layer with ethyl acetate (3×100 mL). The combined ethyl acetate layers were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified on a 110 g SiO2 cartridge using ethyl acetate/hexanes gradient to give (±)-cis-4-hydroxymethyl-3-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester (10.2 g).