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

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Reaction Steps

A 10 mL Schlenk flask was charged with bis(sulfonamide) ligand 2 (3.8 mg, 0.01 mmol), Ti(OtBu)4 (193 μL, 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 μL, 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. 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 (CDCl3, 500 MHz) δ.1.20 (d, 3H, J=6.2 Hz), 1.51 (m, 4H), 1.61 (br s, 1H), 1.99 (m, 4H), 4.10 (q, 1H, J=6.2 Hz), and 5.61 (br t, 1H) ppm; 13C{1H} NMR (CDCl3; 125 MHz) δ.21.4, 22.5, 22.6, 23.6, 24.8, 72.0, 121.3, and 141.2 ppm. 1H NMR and 13C NMR spectra for this compound compare with previously reported literature data.

Provenance & Evidence