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

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Reaction Steps

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)

Provenance & Evidence