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

Participants

Reaction Steps

By the procedure for entry 9 of Table 1, the reaction of sodium phenoxide (232 mg, 2.00 mmol) and ethyl cinnamyl carbonate (192 mg, 0.930 mmol) with [(COD)IrCl]2 (6.7 mg, 0.010 mmol) and L1 (Sa,Sc,Sc) (10.8 mg, 0.0200 mmol) as catalyst was conducted at room temperature for 32 h. 1H NMR analysis of the crude reaction showed the ratios of branched to linear products to be 99/1. After purification, 159 mg of the title compound (75%) was isolated. HPLC analysis as described above indicated that the enantiomeric excess of the major product was 94%.

Provenance & Evidence