Aniline → Benzenamine, N-2-cyclohexen-1-yl-

Twelve enantioselective Examples are shown in Table 5 below (entries 1-12). A typical procedure is as follows: [Pd(π-allyl)Cl]2 (2.3 mg, 0.0063 mmol) and the (R,R)-Naphthyl-Trost ligand (10.9 mg, 0.0138 mmol) were dissolved in 0.1 mL of dry THF in a screw-capped vial. After stirring for one min, aniline (11.4 μL, 0.125 mmol) was added, and the color of the solution turned bright yellow. After addition of cyclohexadiene (47.6 μL, 0.500 mmol), the vial was sealed with a cap that contained a PTFE septum, and the reaction mixture was stirred at room temperature for 120 h. After removal of all volatile compounds using a rotary evaporator, the residue was purified by chromatography on silica gel (Hexanes : EtOAc=200:1) to give 18.8 mg (87%) of N-cyclohex-2-en-1-ylaniline as a colorless oil with 89% ee and the [α]D24° C. value of −84.5 (c 1.0222, CH2Cl2)

1. customthe vial was sealed with
2. customa cap that
3. stirringthe reaction mixture was stirred at room temperature for 120 h
4. customAfter removal of all volatile compounds
5. customa rotary evaporator
6. customthe residue was purified by chromatography on silica gel (Hexanes : EtOAc=200:1)

ORD record

ord-5688680ff0164d2fbe5530ede66a01e8

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06384282B2