Benzylamine → (-)-1-Methoxy-4-(1-propylallyloxy)benzene

Participants

Reaction Steps

Reaction of benzylamine with methyl cinnamyl carbonate catalyzed by Complex Ir-3 and [(COE)2IrCl]2 (FIG. 2, triangles): By the procedure for reaction of the combination of Ir-2 and [(COD)IrCl]2, the reaction of benzylamine (135 mg, 1.26 mmol) and methyl cinnamyl carbonate (192 mg, 1.00 mmol) catalyzed by [(COD)Ir(κ2-L1)(PPh3)] (Ir-3) (11.0 mg, 0.0100 mmol) and [(COE)2IrCl]2 (4.4 mg, 0.0050 mmol) was monitored by GC for 10 h. 1H NMR analysis of the crude reaction showed the ratios of products to be 98/1/1, and after purification of the product by the general procedure, HPLC analysis as described above indicated that the enantiomeric excess of the major product was 97.2%.

Provenance & Evidence