Stereoselective Homocoupling of Enolate Anion Promoted by Hypervalent Iodine Compound

References

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• Typically, in a 50 mL round bottomed flask, 2a (500 mg, 2.14 mmol) was dissolved in 6 mL THF under nitrogen. LHMDS (2.36 mmol) and (diacetoxyiodo)benzene (4.29 mmol) were added to the solution sequencially at −78°C. The solution was warmed to 0°C after 1 hr. The reaction was stopped by adding water after 1hr. The product was extracted by dichloromethane. The organic layer was dried by sodium sulfate. The residue after evaporation of solvent was chromatographed with silica gel using hexane and ethylacetate. Total yield was 86%. (2R,3S)-4a: mp 182–184°C, 1H-NMR (CDCl3, 400 MHz) δ 7.36–7.20 (10H, m), 4.71–4.63 (2H, m), 4.30–4.11 (6H, m), 3.47 (1H, dd, J = 3.3, 13.3 Hz), 3.25 (1H, dd, J = 3.40, 13.4 Hz), 2.85–2.69 (2H, m), 1.28–1.30 (6H, m), MS (El) m/z 464 (M+). (2R,3R)-4a: mp 156–158°C, 1H-NMR (CDCl3, 400 MHz) δ 7.31–7.20 (10H, m), 4.68–4.62 (2H, m), 4.2–4.09 (6H, m), 3.14 (2H, dd, J = 3.2, 13.2 Hz), 2.82 (2H, dd, J = 9.0, 13.8 Hz), 1.30 (6H, d, J = 6.39 Hz), MS (El) m/z 464 (M+)
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