Acid-promoted reaction of sulfonyl chlorides with alkenes: New approach to the regioselective synthesis of β-hydroxyl sulfone derivatives

Synlett

Volumn , Issue 9, 2004, Pages 1595-1597

  Xi, Chanjuan ^a   Lai, Chunbo ^a   Chen, Chao ^a   Wang, Ruji ^a  

^a TSINGHUA UNIVERSITY   (China)

Author keywords

Acid catalyzed; Alkene; Hydroxyl sulfonylation reaction; Sulfone; Sulfonyl chloride

Indexed keywords

ACID; ALKENE; BETA HYDROXYSULFONE DERIVATIVE; CHLORIDE; SULFONE DERIVATIVE; SULFONIC ACID DERIVATIVE; SULFONYL CHLORIDE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; SYNTHESIS;

EID: 3943093192     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829090     Document Type: Article

References (37)

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14. For representative examples of Cu(I)-catalyzed addition of sulfonyl chlorides to alkenes, see: (a) Asscher, M.; Vofsi, D. J. Chem. Soc. 1964, 4962. (b) Orochov, A.; Asscher, M.; Vofsi, D. J. Chem. Soc. B 1969, 255. (c) Sinnreich, J.; Asscher, M. J. Chem. Soc., Perkin Trans. 1 1972, 1543. (d) Orochov, A.; Asscher, M.; Vofsi, D. J. Chem. Soc., Perkin Trans. 2 1973, 1000. (e) Da Silva Correa, C. M. M.; Waters, A. J. Chem. Soc. C 1968, 1874. (f) Ameil, Y. J. Org. Chem. 1974, 39, 3867. (g) Percec, V.; Barboiu, B.; Kim, H.-J. J. Am. Chem. Soc. 1998, 120, 305.
15. For representative examples of Cu(I)-catalyzed addition of sulfonyl chlorides to alkenes, see: (a) Asscher, M.; Vofsi, D. J. Chem. Soc. 1964, 4962. (b) Orochov, A.; Asscher, M.; Vofsi, D. J. Chem. Soc. B 1969, 255. (c) Sinnreich, J.; Asscher, M. J. Chem. Soc., Perkin Trans. 1 1972, 1543. (d) Orochov, A.; Asscher, M.; Vofsi, D. J. Chem. Soc., Perkin Trans. 2 1973, 1000. (e) Da Silva Correa, C. M. M.; Waters, A. J. Chem. Soc. C 1968, 1874. (f) Ameil, Y. J. Org. Chem. 1974, 39, 3867. (g) Percec, V.; Barboiu, B.; Kim, H.-J. J. Am. Chem. Soc. 1998, 120, 305.
16. For representative examples of Cu(I)-catalyzed addition of sulfonyl chlorides to alkenes, see: (a) Asscher, M.; Vofsi, D. J. Chem. Soc. 1964, 4962. (b) Orochov, A.; Asscher, M.; Vofsi, D. J. Chem. Soc. B 1969, 255. (c) Sinnreich, J.; Asscher, M. J. Chem. Soc., Perkin Trans. 1 1972, 1543. (d) Orochov, A.; Asscher, M.; Vofsi, D. J. Chem. Soc., Perkin Trans. 2 1973, 1000. (e) Da Silva Correa, C. M. M.; Waters, A. J. Chem. Soc. C 1968, 1874. (f) Ameil, Y. J. Org. Chem. 1974, 39, 3867. (g) Percec, V.; Barboiu, B.; Kim, H.-J. J. Am. Chem. Soc. 1998, 120, 305.
17. For representative examples of Cu(I)-catalyzed addition of sulfonyl chlorides to alkenes, see: (a) Asscher, M.; Vofsi, D. J. Chem. Soc. 1964, 4962. (b) Orochov, A.; Asscher, M.; Vofsi, D. J. Chem. Soc. B 1969, 255. (c) Sinnreich, J.; Asscher, M. J. Chem. Soc., Perkin Trans. 1 1972, 1543. (d) Orochov, A.; Asscher, M.; Vofsi, D. J. Chem. Soc., Perkin Trans. 2 1973, 1000. (e) Da Silva Correa, C. M. M.; Waters, A. J. Chem. Soc. C 1968, 1874. (f) Ameil, Y. J. Org. Chem. 1974, 39, 3867. (g) Percec, V.; Barboiu, B.; Kim, H.-J. J. Am. Chem. Soc. 1998, 120, 305.
18. For representative examples of Cu(I)-catalyzed addition of sulfonyl chlorides to alkenes, see: (a) Asscher, M.; Vofsi, D. J. Chem. Soc. 1964, 4962. (b) Orochov, A.; Asscher, M.; Vofsi, D. J. Chem. Soc. B 1969, 255. (c) Sinnreich, J.; Asscher, M. J. Chem. Soc., Perkin Trans. 1 1972, 1543. (d) Orochov, A.; Asscher, M.; Vofsi, D. J. Chem. Soc., Perkin Trans. 2 1973, 1000. (e) Da Silva Correa, C. M. M.; Waters, A. J. Chem. Soc. C 1968, 1874. (f) Ameil, Y. J. Org. Chem. 1974, 39, 3867. (g) Percec, V.; Barboiu, B.; Kim, H.-J. J. Am. Chem. Soc. 1998, 120, 305.
19. For peroxide-induced addition of sulfonyl chlorides to alkenes, see: Kharash, M. S.; Zavist, A. F. J. Am. Chem. Soc. 1951, 73, 964.
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21. For selected examples of Ru(II)-catalyzed addition of sulfonyl chlorides to alkenes, see: (a) Kamigata, N.; Sawada, H.; Kobayashi, M. Chem. Lett. 1979, 159. (b) Kamigata, N.; Sawada, H.; Kobayashi, M. J. Org. Chem. 1983, 48, 3793. (c) Kamigata, N.; Ozaki, J.; Kobayashi, M. J. Org. Chem. 1985, 50, 5045. (d) Kamigata, N.; Fukushima, T.; Terakawa, Y.; Yoshida, M.; Sawada, H. J. Chem. Soc., Perkin Trans. 1 1991, 627. (e) Kameyama, M.; Kamigata, N.; Kobayashi, M. Chem. Lett. 1986, 527. (f) Kameyama, M.; Kamigata, N. Bull. Chem. Soc. Jpn. 1989, 62, 648.
22. For selected examples of Ru(II)-catalyzed addition of sulfonyl chlorides to alkenes, see: (a) Kamigata, N.; Sawada, H.; Kobayashi, M. Chem. Lett. 1979, 159. (b) Kamigata, N.; Sawada, H.; Kobayashi, M. J. Org. Chem. 1983, 48, 3793. (c) Kamigata, N.; Ozaki, J.; Kobayashi, M. J. Org. Chem. 1985, 50, 5045. (d) Kamigata, N.; Fukushima, T.; Terakawa, Y.; Yoshida, M.; Sawada, H. J. Chem. Soc., Perkin Trans. 1 1991, 627. (e) Kameyama, M.; Kamigata, N.; Kobayashi, M. Chem. Lett. 1986, 527. (f) Kameyama, M.; Kamigata, N. Bull. Chem. Soc. Jpn. 1989, 62, 648.
23. For selected examples of Ru(II)-catalyzed addition of sulfonyl chlorides to alkenes, see: (a) Kamigata, N.; Sawada, H.; Kobayashi, M. Chem. Lett. 1979, 159. (b) Kamigata, N.; Sawada, H.; Kobayashi, M. J. Org. Chem. 1983, 48, 3793. (c) Kamigata, N.; Ozaki, J.; Kobayashi, M. J. Org. Chem. 1985, 50, 5045. (d) Kamigata, N.; Fukushima, T.; Terakawa, Y.; Yoshida, M.; Sawada, H. J. Chem. Soc., Perkin Trans. 1 1991, 627. (e) Kameyama, M.; Kamigata, N.; Kobayashi, M. Chem. Lett. 1986, 527. (f) Kameyama, M.; Kamigata, N. Bull. Chem. Soc. Jpn. 1989, 62, 648.
24. For selected examples of Ru(II)-catalyzed addition of sulfonyl chlorides to alkenes, see: (a) Kamigata, N.; Sawada, H.; Kobayashi, M. Chem. Lett. 1979, 159. (b) Kamigata, N.; Sawada, H.; Kobayashi, M. J. Org. Chem. 1983, 48, 3793. (c) Kamigata, N.; Ozaki, J.; Kobayashi, M. J. Org. Chem. 1985, 50, 5045. (d) Kamigata, N.; Fukushima, T.; Terakawa, Y.; Yoshida, M.; Sawada, H. J. Chem. Soc., Perkin Trans. 1 1991, 627. (e) Kameyama, M.; Kamigata, N.; Kobayashi, M. Chem. Lett. 1986, 527. (f) Kameyama, M.; Kamigata, N. Bull. Chem. Soc. Jpn. 1989, 62, 648.
25. For selected examples of Ru(II)-catalyzed addition of sulfonyl chlorides to alkenes, see: (a) Kamigata, N.; Sawada, H.; Kobayashi, M. Chem. Lett. 1979, 159. (b) Kamigata, N.; Sawada, H.; Kobayashi, M. J. Org. Chem. 1983, 48, 3793. (c) Kamigata, N.; Ozaki, J.; Kobayashi, M. J. Org. Chem. 1985, 50, 5045. (d) Kamigata, N.; Fukushima, T.; Terakawa, Y.; Yoshida, M.; Sawada, H. J. Chem. Soc., Perkin Trans. 1 1991, 627. (e) Kameyama, M.; Kamigata, N.; Kobayashi, M. Chem. Lett. 1986, 527. (f) Kameyama, M.; Kamigata, N. Bull. Chem. Soc. Jpn. 1989, 62, 648.
26. 2 = 0.1519 (all data), GOF = 1.053.
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30. +].
31. +].
32. +].
33. +].
34. +].
35. 3S: 234.0117, 236.0088; found: 234.0111, 236.0046.
36. 3S: 214.0664; found: 214.0665.
37. +].