Isobutyraldehyde → HCID 5166296, compound

Participants

Reaction Steps

In a dry, argon flushed 5 mL flask, equipped with a magnetic stirrer and a septum, CuBr (1.5 mg, 0.01 mmol, 5 mol %) and (R)(+)-FLiNAP (5.7 mg, 0.011 mmol, 5.5 mol %) were suspended in dry toluene (1 mL) and stirred for 30 min. Phenylacetylene (9) (21 mg, 0.2 mmol), 2-methylpropanal (7) (15 mg, 0.2 mmol) and dibenzylamine (8) (40 mg, 0.2 mmol) were then added. The reaction mixture was stirred at room temperature for 2 days. The crude product was concentrated under reduced pressure and purified by column chromatography on silica gel (95:5 pentane/ether) to yield the title compound 10 as an enantiomeric mixture. The enantiomers were subsequently separated using HPLC [(Chiralcel OD-H, 99% n-heptane/1% i-propanol, 0.2 mL/min): t, (min)=19.94 (−), 20.98 (+)]. The (−) isomer was isolated as an oil (60 mg, 85% yield, 87% ee).

Provenance & Evidence