References
- Present address: Department of Chemistry, Pohang University of Science and Technology, San 31, Hyoja-dong, Namgu, Pohang 790–784, KOREA
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- General procedure for the synthesis of α-methyl vinyl sulfones via Horner-Emmons reaction: A solution of ethyl phenyl sulfone (1 mmol) in 6mL of anhydrous THF was treated dropwise with a solution of 1.6 Mn-BuLi (2 mmol) in hexane at 0°C. After 30min of stirring at 0°C, the suspended reagent was treated dropwise with a solution of diethyl chlorophosphate (1 mmol) in 2 mL of THF. The reaction mixture was stirred for 30 min at 0°C. To the resulting yellow solution, aldehyde (1 mmol) was added and stirred for 1 hr at 0°C. Normal work-up was performed. The vinyl sulfone was purified by column chromatography on silica gel using EtOAc/ hexanes (1/9) as an eluent. 1H NMR (200 MHz, CDCl3) 5a δ 2.23 (s, 3H), 7.37 (s, 5H), 7.40–7.59 (m, 3H), 7.60–8.0 (m, 3H); 5b δ 2.09 (s, 3H), 3.80 (s, 3H), 6.90 (d, J = 8.77, 2H), 7.36 (d, J = 8.77, 2H) 7.47–7.60 (m, 3H), 7.74 (s, 1H), 7.88 (d, J = 5.5, 2H); 5c δ 2.09 (s, 3H), 7.45–7.70 (m, 5H), 7.80 (s, 1H), 7.89 (d, J = 7.75, 2H), 8.14–8.18 (m, 2H); 5d δ 1.91 (s, 3H), 6.70–6.90 (m, 2H), 7.20–7.26 (m, 3H), 7.30–7.52 (m, 6H), 7.76–7.81 (m, 2H); 5e δ 1.71 (d, J = 7.0, 3H), 2.08 (s, 3H), 7.54–7.62 (m, 2H), 7.46–7.61 (m, 2H), 7.95–8.0(m, 2H).