New carbon-carbon bond formation through oxyallylation of enoxysilanes with sulfur dioxide adduct of 1-methoxybutadiene. Stereoselective synthesis of (Z)-4-methoxy-6-oxoalk-2-enyl methyl sulfones

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6197-6200

  Deguin, Brigitte ^a,c   Roulet, Jean Michel ^b,c   Vogel, Pierre ^c  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b UNIVERSITÉ DE SHERBROOKE   (Canada)

^c UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

4 METHOXY 6 OXOALK 2 ENYL METHYL SULFONE DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; DIASTEREOISOMER; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030791394     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01397-X     Document Type: Article

References (28)

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3. Deguin, B.; Vogel, P. Tetrahedron Lett. 1993, 34, 6269-6270; see also: Heldeweg, R. F.; Hogeveen, H. J. Am. Chem. Soc. 1976, 98, 2341-2342; Durst, T.; Tétreault-Ryan, L. Tetrahedron Lett. 1978, 2353-2354.
4. Deguin, B.; Vogel, P. Tetrahedron Lett. 1993, 34, 6269-6270; see also: Heldeweg, R. F.; Hogeveen, H. J. Am. Chem. Soc. 1976, 98, 2341-2342; Durst, T.; Tétreault-Ryan, L. Tetrahedron Lett. 1978, 2353-2354.
5. Woodward, R. B.; Hoffmann, R. "The Conservation of Orbital Symmetry", Academic Press, New York, 1970; Turk, S. D.; Cobb, R. L. in "1,4-Cycloaddition Reactions", Hamer, J., Ed.; Academic Press, New York, 1967, p. 13; Dewar, M. J. S. J. Am. Chem. Soc. 1984, 106, 209-219 and preceeding papers.
6. Woodward, R. B.; Hoffmann, R. "The Conservation of Orbital Symmetry", Academic Press, New York, 1970; Turk, S. D.; Cobb, R. L. in "1,4-Cycloaddition Reactions", Hamer, J., Ed.; Academic Press, New York, 1967, p. 13; Dewar, M. J. S. J. Am. Chem. Soc. 1984, 106, 209-219 and preceeding papers.
7. Woodward, R. B.; Hoffmann, R. "The Conservation of Orbital Symmetry", Academic Press, New York, 1970; Turk, S. D.; Cobb, R. L. in "1,4-Cycloaddition Reactions", Hamer, J., Ed.; Academic Press, New York, 1967, p. 13; Dewar, M. J. S. J. Am. Chem. Soc. 1984, 106, 209-219 and preceeding papers.
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10. De Bruin, G. Proc. K. Ned. Akad. Wet. 1914, 17, 585-543; Backer, H. J.; Strating, J. Recl. Trav. Chim. Pays-Bas 1934, 53, 525-543; 1943, 62, 815-823.
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14. All the new compounds were fully characterized by their spectral data and gave satisfactory elemental analyses.
15. 1J(C,H)=158 C(4)), 136.7 (s), 133.4, 128.7, 128.1 (d, 161), 119.5 (d, 164, C(5)), 73.1 (d, 145, C(3)), 56.6 (q, MeO), 54.0 (t, 136, C(6)), 43.0 (t, 128, C(2), 40.1 (q, 138, Me).
16. Nakamura, E.; Hashimoto, K.; Kuwajima, I. Tetrahedron Lett. 1978, 24, 2079.
17. 3J=7.2).
18. Brown, H. C.; Krishnamurphy, S. Aldrichimica Acta 1979, 12, 3-7; see for e.g.: Knapp, S.; Levorse, A. T. J. Org. Chem. 1988, 53, 4006-4014.
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20. 3J=12.7, 5.4, 4.8, 1H), 2.40-1.50 (m, 8H).
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22. See e.g.: Braverman, S. in "The Chemistry of Sulfinic Acids, Esters and their Derivatives" Patai, S.; Rappoport, Z.; Stirling, C. J. M., Eds., J. Wiley & Sons, Chichester, 1990, p. 298; Mock, W. L.; Nugent, R. M. J. Org. Chem. 1978, 43, 3433-3434; Baudin, J. B.; Julia, S. Bull. Soc. Chim. Fr. 1995, 132, 196- 214 and ref. cited therein.
23. See e.g.: Braverman, S. in "The Chemistry of Sulfinic Acids, Esters and their Derivatives" Patai, S.; Rappoport, Z.; Stirling, C. J. M., Eds., J. Wiley & Sons, Chichester, 1990, p. 298; Mock, W. L.; Nugent, R. M. J. Org. Chem. 1978, 43, 3433-3434; Baudin, J. B.; Julia, S. Bull. Soc. Chim. Fr. 1995, 132, 196- 214 and ref. cited therein.
24. See e.g.: Braverman, S. in "The Chemistry of Sulfinic Acids, Esters and their Derivatives" Patai, S.; Rappoport, Z.; Stirling, C. J. M., Eds., J. Wiley & Sons, Chichester, 1990, p. 298; Mock, W. L.; Nugent, R. M. J. Org. Chem. 1978, 43, 3433-3434; Baudin, J. B.; Julia, S. Bull. Soc. Chim. Fr. 1995, 132, 196-214 and ref. cited therein.
25. See e.g.: Mukaiyama, T. Org. React. 1982, 28, 203-331; Heathcock, C. H.; Davidsen, S. K.; Hug, K. T.; Flippin, L. A. J. Org. Chem. 1986, 51, 3027-3037.
26. See e.g.: Mukaiyama, T. Org. React. 1982, 28, 203-331; Heathcock, C. H.; Davidsen, S. K.; Hug, K. T.; Flippin, L. A. J. Org. Chem. 1986, 51, 3027-3037.
27. Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106-2108.
28. Noyori, R.; Yokoyama, K.; Sakata, J.; Kuwajima, I.; Nakamura, E.; Shimizu, M. J. Am. Chem. Soc. 1977, 99, 1265-1267.