One-Pot Synthesis of α-Methyl Vinyl Sulfones From Ethyl Phenyl Sulfones

References

• Present address: Department of Chemistry, Pohang University of Science and Technology, San 31, Hyoja-dong, Namgu, Pohang 790–784, KOREA
   Google Scholar
• Fuchs , P. L. and Braish , T. F. 1986 . Chem. Rev. , 86 : 903 (b) De Lucci, O. and Pasquato, L. Tetrahedron 1988, 44, 6755.
   Web of Science ®Google Scholar
• Popoff , I. C. , Denver , J. L. and Leader , G. R. 1969 . J. Org. Chem. , 34 : 1128
   Web of Science ®Google Scholar
• Ley , S. V. and Simpkins , N. S. 1983 . J. Chem. Soc., Chem. Commun. , : 1281 (b) Ager, D.J. J. Chem. Soc., Chem. Commun., 1984, 486.
   Google Scholar
• Gancarz , R. A. and Kice , J. L. 1980 . Tetrahedron Lett. , : 4155
   Google Scholar
• Asscher , M. and Vofsi , D. 1964 . J. Chem. Soc. , : 4962 (b) Asscher, M. and Vofsi, D., J. Chem. Soc., Perkin Trans 1, 1972, 1543. (c) Hopkins, P. B. and Fuchs, P. L. J. Org. Chem. 1978, 43, 1208.
   Web of Science ®Google Scholar
• Lee , J. W. and Oh , D. Y. 1989 . Synth. Commun. , 19 : 2209 (b) Lee, J. W. and Oh, D. Y. Bull. Korean Chem. Soc., 1989, 10, 39. (c) Lee, J. W. and Oh, D. Y. Synth. Commun. 1990, 20, 273.
   Web of Science ®Google Scholar
• Kaiser , E. M. , Solter , L. E. , Schwartz , R. A. , Beard , R. D. and Harser , C. R. 1971 . J. Am. Chem. Soc. , 93 : 423 (b) Trost, B. M.; Schmuff, N. R. and Miller, M. J. J. Am. Chem. Soc., 1980, 102, 5979. (c) Trost, B. M. and Merlic, C. A. J. Am. Chem. Soc., 1988, 110, 5216. (d) Gais, H. J. and Vollhardt, J. Tetrahedron Lett. 1988, 1529. (e) Hendrickson, J. B.; Boudreaux, G. J. and Palumbo, P. S., J. Am. Chem. Soc., 1986, 108, 2358. (f) Vollhardt, J.; Gais, H. J. and Lukas, K. L. Angew. Chem. Int. Ed. Engl., 1985, 24, 696. (g) Idem, ibid, 1985, 24, 610. (h) Kondo, K. and Tunemoto, D. Tetrahedron Lett. 1975, 1397.
   Google Scholar
• 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).
   Google Scholar