Ethyl cinnamyl carbonate → 1-Phenyl-1-phenoxy-2-propene

Participants

Reaction Steps

[(COD)Ir(κ2-L1)(L1)] (Ir-2) (13.8 mg, 0.0100 mmol), [(COD)IrCl]2 (3.4 mg, 0.0050 mmol) and sodium phenoxide (232 mg, 2.00 mmol) were dissolved in 1.0 mL of THF. Ethyl cinnamyl carbonate (192 mg, 0.930 mmol) was added to the reaction mixture by syringe. After being stirred at room temperature for 2 h, the reaction mixture was poured into brine, extracted with ether, dried, filtered, and concentrated. 1H NMR analysis of the mixture indicated that the ratio of branched to linear regioisomers was 95/5. The residue was purified by flash chromatography on silica gel (1% Et2O/Hexanes) to afford 157 mg (75%) of 1-phenyl-1-phenoxy-2-propene as a viscous oil. [Rf 0.85 (5% Et2O/Hexanes)] HPLC analysis indicated an enantiomeric excess of 94% [Chiralcel® OJ-H column, eluting with 99.75/0.25 hexane/i-PrOH, 0.6 mL/min, 220 nm; major enantiomer TR, 45.4, minor enantiomer TR 55.3 min]; [α]D20=+8.9 (c 1.4, CHCl3); 1H NMR (500.13 MHz, CDCl3) δ 7.48-7.27 (m, 8H), 7.01-6.96 (m, 2H), 6.15 (ddd, J=17.2, 10.4, 5.9 Hz, 1H), 5.70 (d, J=5.9 Hz, 1H), 5.41 (d, J=17.2 Hz, 1H), 5.31 (d, J=10.4 Hz, 1H). 13C NMR (125.7 MHz, CDCl3) δ 157.9 (C), 140.1 (C), 137.9 (CH), 129.3 (CH), 128.6 (CH), 127.8 (CH), 126.6 (CH), 121.0 (CH), 116.5 (CH2), 116.2 (CH), 80.8 (CH).

Provenance & Evidence