1-Cyclohexene-1-carboxaldehyde → HCID 11018877, compound

Participants

Reaction Steps

A 10 mL Schlenk flask was charged with bis(sulfonamide) ligand L*2 (3.8 mg, 0.01 mmol), Ti(OtBu)4 (193 □L, 0.50 mmol), and 0.5 mL hexanes and stirred for 30 min at room temp. A hexanes solution of Me2Zn (0.32 mL, 0.63 mmol) was then added, and after stirring for 10 min, cyclohexenecarboxaldehyde (28 □L, 0.25 mmol) was added. The reaction was stirred at room temp for 19 h and quenched with a saturated solution of aq NH4Cl. The organic and aqueous layers were separated, and the aqueous layer was extracted with hexanes (3×10 mL). The combined organic layers were then washed with brine and H2O and dried over MgSO4. The filtrate was concentrated in vacuo and the residue was chromatographed on silica (10% ethyl acetate in hexanes) to afford the title compound as a colorless oil in 94% yield (30 mg, 0.23 mmol). 1H NMR and 13C{1H} NMR spectra for this compound were identical to the previously reported literature data.

Provenance & Evidence