Highly Stereoselective Nucleophilic Epoxidation of Simple Vinyl Sulfoxides

Journal of Organic Chemistry

Volumn 63, Issue 15, 1998, Pages 4954-4966

  Fernández De La Pradilla, Roberto ^a   Castro, Sonia ^a   Manzano, Pilar ^a   Martín Ortega, María ^a   Priego, Julián ^a   Viso, Alma ^b   Rodríguez, Ana ^c   Fonseca, Isabel ^c  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^c INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0037783633     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972358s     Document Type: Article

References (78)

1. For reviews on the asymmetric epoxidation of allylic alcohols, see: (a) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed. VCH: New York, 1993; p 103. (b) Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1.
2. For reviews on the asymmetric epoxidation of allylic alcohols, see: (a) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed. VCH: New York, 1993; p 103. (b) Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1.
3. For a review on the asymmetric epoxidation of unfunctionalized alkenes, see: Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed. VCH: New York, 1993; p 159.
4. For leading references, see: (a) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 410-412. (b) Enders, D.; Zhu, J.; Kramps, L. Liebigs Ann./Recueil 1997, 1101-1113. (c) Adger, B. M.; Barkley, J. V.; Bergeron, S.; Cappi, M. W.; Flowerdew, B. E.; Jackson, M. P.; McCague, R.; Nugent, T. C.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1997, 3501-3507. (d) Allen, J. V.; Cappi, M. W.; Kary, P. D.; Roberts, S. M.; Williamson, N. M.; Wu, L. E. Ibid. 1997, 3297-3298. (e) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330. For a review on applications of polymeric amino acids to this field, see: (f) Ebrahim, S.; Wills, M. Tetrahedron: Asymmetry 1997, 8, 3163-3173.
5. For leading references, see: (a) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 410-412. (b) Enders, D.; Zhu, J.; Kramps, L. Liebigs Ann./Recueil 1997, 1101-1113. (c) Adger, B. M.; Barkley, J. V.; Bergeron, S.; Cappi, M. W.; Flowerdew, B. E.; Jackson, M. P.; McCague, R.; Nugent, T. C.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1997, 3501-3507. (d) Allen, J. V.; Cappi, M. W.; Kary, P. D.; Roberts, S. M.; Williamson, N. M.; Wu, L. E. Ibid. 1997, 3297-3298. (e) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330. For a review on applications of polymeric amino acids to this field, see: (f) Ebrahim, S.; Wills, M. Tetrahedron: Asymmetry 1997, 8, 3163-3173.
6. For leading references, see: (a) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 410-412. (b) Enders, D.; Zhu, J.; Kramps, L. Liebigs Ann./Recueil 1997, 1101-1113. (c) Adger, B. M.; Barkley, J. V.; Bergeron, S.; Cappi, M. W.; Flowerdew, B. E.; Jackson, M. P.; McCague, R.; Nugent, T. C.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1997, 3501-3507. (d) Allen, J. V.; Cappi, M. W.; Kary, P. D.; Roberts, S. M.; Williamson, N. M.; Wu, L. E. Ibid. 1997, 3297-3298. (e) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330. For a review on applications of polymeric amino acids to this field, see: (f) Ebrahim, S.; Wills, M. Tetrahedron: Asymmetry 1997, 8, 3163-3173.
7. For leading references, see: (a) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 410-412. (b) Enders, D.; Zhu, J.; Kramps, L. Liebigs Ann./Recueil 1997, 1101-1113. (c) Adger, B. M.; Barkley, J. V.; Bergeron, S.; Cappi, M. W.; Flowerdew, B. E.; Jackson, M. P.; McCague, R.; Nugent, T. C.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1997, 3501-3507. (d) Allen, J. V.; Cappi, M. W.; Kary, P. D.; Roberts, S. M.; Williamson, N. M.; Wu, L. E. Ibid. 1997, 3297-3298. (e) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330. For a review on applications of polymeric amino acids to this field, see: (f) Ebrahim, S.; Wills, M. Tetrahedron: Asymmetry 1997, 8, 3163-3173.
8. For leading references, see: (a) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 410-412. (b) Enders, D.; Zhu, J.; Kramps, L. Liebigs Ann./Recueil 1997, 1101-1113. (c) Adger, B. M.; Barkley, J. V.; Bergeron, S.; Cappi, M. W.; Flowerdew, B. E.; Jackson, M. P.; McCague, R.; Nugent, T. C.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1997, 3501-3507. (d) Allen, J. V.; Cappi, M. W.; Kary, P. D.; Roberts, S. M.; Williamson, N. M.; Wu, L. E. Ibid. 1997, 3297-3298. (e) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330. For a review on applications of polymeric amino acids to this field, see: (f) Ebrahim, S.; Wills, M. Tetrahedron: Asymmetry 1997, 8, 3163-3173.
9. For leading references, see: (a) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 410-412. (b) Enders, D.; Zhu, J.; Kramps, L. Liebigs Ann./Recueil 1997, 1101-1113. (c) Adger, B. M.; Barkley, J. V.; Bergeron, S.; Cappi, M. W.; Flowerdew, B. E.; Jackson, M. P.; McCague, R.; Nugent, T. C.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1997, 3501-3507. (d) Allen, J. V.; Cappi, M. W.; Kary, P. D.; Roberts, S. M.; Williamson, N. M.; Wu, L. E. Ibid. 1997, 3297-3298. (e) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330. For a review on applications of polymeric amino acids to this field, see: (f) Ebrahim, S.; Wills, M. Tetrahedron: Asymmetry 1997, 8, 3163-3173.
10. (a) Bailey, P. L.; Clegg, W.; Jackson, R. F. W.; Meth-Cohn, O. J. Chem. Soc., Perkin Trans. 1 1993, 343-350. For related studies, see:
11. (b) Briggs, A. D.; Jackson, R. F. W.; Clegg, W.; Elsegood, M. R. J.; Kelly, J.; Brown, P. A. Tetrahedron Lett. 1994, 35, 6945-6948.
12. (c) Bailey, P. L.; Briggs, A. D.; Jackson, R. F. W.; Pietruszka, J. Tetrahedron Lett. 1993, 41, 6611-6614.
13. For leading references on related nucleophilic epoxidations, see: (a) Jackson, R. F. W.; Turner, D.; Block, M. H. Synlett 1997, 789-790. (b) Clayden, J.; Nelson, A.; Warren, S. Tetrahedron Lett. 1997, 38, 3471-3474. (c) Evans, P.; Taylor, R. J. K. Tetrahedron Lett 1997, 38, 3055. (d) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431-6440. (e) Jackson, R. F. W.; Standen, S. P.; Clegg, W.; McCamley, A. J. Chem. Soc., Perkin Trans. 1 1995, 141-148. (f) Jackson, R. F. W.; Standen, S. P.; Clegg, W. J. Chem. Soc., Perkin Trans. 1 1995, 149-156. (g) Linderman, R. J.; Claassen, R. J., II.; Viviani, F. Tetrahedron Lett. 1995, 36, 6611-6614. (h) Yoshimatsu, M.; Gotoh, S.; Gotoh, E.; Tanabe, G.; Muraoka, O. J. Chem. Soc., Perkin Trans. 1 1997, 3035-3041.
14. For leading references on related nucleophilic epoxidations, see: (a) Jackson, R. F. W.; Turner, D.; Block, M. H. Synlett 1997, 789-790. (b) Clayden, J.; Nelson, A.; Warren, S. Tetrahedron Lett. 1997, 38, 3471-3474. (c) Evans, P.; Taylor, R. J. K. Tetrahedron Lett 1997, 38, 3055. (d) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431-6440. (e) Jackson, R. F. W.; Standen, S. P.; Clegg, W.; McCamley, A. J. Chem. Soc., Perkin Trans. 1 1995, 141-148. (f) Jackson, R. F. W.; Standen, S. P.; Clegg, W. J. Chem. Soc., Perkin Trans. 1 1995, 149-156. (g) Linderman, R. J.; Claassen, R. J., II.; Viviani, F. Tetrahedron Lett. 1995, 36, 6611-6614. (h) Yoshimatsu, M.; Gotoh, S.; Gotoh, E.; Tanabe, G.; Muraoka, O. J. Chem. Soc., Perkin Trans. 1 1997, 3035-3041.
15. For leading references on related nucleophilic epoxidations, see: (a) Jackson, R. F. W.; Turner, D.; Block, M. H. Synlett 1997, 789-790. (b) Clayden, J.; Nelson, A.; Warren, S. Tetrahedron Lett. 1997, 38, 3471-3474. (c) Evans, P.; Taylor, R. J. K. Tetrahedron Lett 1997, 38, 3055. (d) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431-6440. (e) Jackson, R. F. W.; Standen, S. P.; Clegg, W.; McCamley, A. J. Chem. Soc., Perkin Trans. 1 1995, 141-148. (f) Jackson, R. F. W.; Standen, S. P.; Clegg, W. J. Chem. Soc., Perkin Trans. 1 1995, 149-156. (g) Linderman, R. J.; Claassen, R. J., II.; Viviani, F. Tetrahedron Lett. 1995, 36, 6611-6614. (h) Yoshimatsu, M.; Gotoh, S.; Gotoh, E.; Tanabe, G.; Muraoka, O. J. Chem. Soc., Perkin Trans. 1 1997, 3035-3041.
16. For leading references on related nucleophilic epoxidations, see: (a) Jackson, R. F. W.; Turner, D.; Block, M. H. Synlett 1997, 789-790. (b) Clayden, J.; Nelson, A.; Warren, S. Tetrahedron Lett. 1997, 38, 3471-3474. (c) Evans, P.; Taylor, R. J. K. Tetrahedron Lett 1997, 38, 3055. (d) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431-6440. (e) Jackson, R. F. W.; Standen, S. P.; Clegg, W.; McCamley, A. J. Chem. Soc., Perkin Trans. 1 1995, 141-148. (f) Jackson, R. F. W.; Standen, S. P.; Clegg, W. J. Chem. Soc., Perkin Trans. 1 1995, 149-156. (g) Linderman, R. J.; Claassen, R. J., II.; Viviani, F. Tetrahedron Lett. 1995, 36, 6611-6614. (h) Yoshimatsu, M.; Gotoh, S.; Gotoh, E.; Tanabe, G.; Muraoka, O. J. Chem. Soc., Perkin Trans. 1 1997, 3035-3041.
17. For leading references on related nucleophilic epoxidations, see: (a) Jackson, R. F. W.; Turner, D.; Block, M. H. Synlett 1997, 789-790. (b) Clayden, J.; Nelson, A.; Warren, S. Tetrahedron Lett. 1997, 38, 3471-3474. (c) Evans, P.; Taylor, R. J. K. Tetrahedron Lett 1997, 38, 3055. (d) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431-6440. (e) Jackson, R. F. W.; Standen, S. P.; Clegg, W.; McCamley, A. J. Chem. Soc., Perkin Trans. 1 1995, 141-148. (f) Jackson, R. F. W.; Standen, S. P.; Clegg, W. J. Chem. Soc., Perkin Trans. 1 1995, 149-156. (g) Linderman, R. J.; Claassen, R. J., II.; Viviani, F. Tetrahedron Lett. 1995, 36, 6611-6614. (h) Yoshimatsu, M.; Gotoh, S.; Gotoh, E.; Tanabe, G.; Muraoka, O. J. Chem. Soc., Perkin Trans. 1 1997, 3035-3041.
18. For leading references on related nucleophilic epoxidations, see: (a) Jackson, R. F. W.; Turner, D.; Block, M. H. Synlett 1997, 789-790. (b) Clayden, J.; Nelson, A.; Warren, S. Tetrahedron Lett. 1997, 38, 3471-3474. (c) Evans, P.; Taylor, R. J. K. Tetrahedron Lett 1997, 38, 3055. (d) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431-6440. (e) Jackson, R. F. W.; Standen, S. P.; Clegg, W.; McCamley, A. J. Chem. Soc., Perkin Trans. 1 1995, 141-148. (f) Jackson, R. F. W.; Standen, S. P.; Clegg, W. J. Chem. Soc., Perkin Trans. 1 1995, 149-156. (g) Linderman, R. J.; Claassen, R. J., II.; Viviani, F. Tetrahedron Lett. 1995, 36, 6611-6614. (h) Yoshimatsu, M.; Gotoh, S.; Gotoh, E.; Tanabe, G.; Muraoka, O. J. Chem. Soc., Perkin Trans. 1 1997, 3035-3041.
19. For leading references on related nucleophilic epoxidations, see: (a) Jackson, R. F. W.; Turner, D.; Block, M. H. Synlett 1997, 789-790. (b) Clayden, J.; Nelson, A.; Warren, S. Tetrahedron Lett. 1997, 38, 3471-3474. (c) Evans, P.; Taylor, R. J. K. Tetrahedron Lett 1997, 38, 3055. (d) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431-6440. (e) Jackson, R. F. W.; Standen, S. P.; Clegg, W.; McCamley, A. J. Chem. Soc., Perkin Trans. 1 1995, 141-148. (f) Jackson, R. F. W.; Standen, S. P.; Clegg, W. J. Chem. Soc., Perkin Trans. 1 1995, 149-156. (g) Linderman, R. J.; Claassen, R. J., II.; Viviani, F. Tetrahedron Lett. 1995, 36, 6611-6614. (h) Yoshimatsu, M.; Gotoh, S.; Gotoh, E.; Tanabe, G.; Muraoka, O. J. Chem. Soc., Perkin Trans. 1 1997, 3035-3041.
20. For leading references on related nucleophilic epoxidations, see: (a) Jackson, R. F. W.; Turner, D.; Block, M. H. Synlett 1997, 789-790. (b) Clayden, J.; Nelson, A.; Warren, S. Tetrahedron Lett. 1997, 38, 3471-3474. (c) Evans, P.; Taylor, R. J. K. Tetrahedron Lett 1997, 38, 3055. (d) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431-6440. (e) Jackson, R. F. W.; Standen, S. P.; Clegg, W.; McCamley, A. J. Chem. Soc., Perkin Trans. 1 1995, 141-148. (f) Jackson, R. F. W.; Standen, S. P.; Clegg, W. J. Chem. Soc., Perkin Trans. 1 1995, 149-156. (g) Linderman, R. J.; Claassen, R. J., II.; Viviani, F. Tetrahedron Lett. 1995, 36, 6611-6614. (h) Yoshimatsu, M.; Gotoh, S.; Gotoh, E.; Tanabe, G.; Muraoka, O. J. Chem. Soc., Perkin Trans. 1 1997, 3035-3041.
21. (a) Fernández de la Pradilla, R.; Martínez, M. V.; Montero, C.; Viso, A. Tetrahedron Lett. 1997, 38, 7773-7776.
22. (b) Paley, R. S.; de Dios, A.; Estroff, L. A.; Lafontaine, J. A.; Montero, C.; McCulley, D. J.; Rubio, M. B.; Ventura, M. P.; Weers, H. L.; Fernández de la Pradilla, R.; Castro, S.; Dorado, R.; Morente, M. J. Org. Chem. 1997, 62, 6326-6343.
23. (c) Viso, A.; Fernández de la Pradilla, R.; Guerrero-Strachan, C.; Alonso, M.; Martínez-Ripoll, M.; André, I. J. Org. Chem. 1997, 62, 2316-2317.
24. (d) Marino, J. P.; Viso, A.; Lee, J.-D.; Fernández de la Pradilla, R.; Fernández, P.; Rubio, M. B. J. Org. Chem. 1997, 62, 645-653.
25. (e) Paley, R. S.; Rubio, M. B.; Fernández de la Pradilla, R.; Dorado, R.; Hundal, G.; Martínez-Ripoll, M. Organometallics 1996, 15, 4672-4674.
26. (f) Marino, J. P.; Anna, L. J.; Fernández de la Pradilla, R.; Martínez, M. V.; Montero, C.; Viso, A. Tetrahedron Lett. 1996, 37, 8031-8034.
27. (g) Arjona, O.; Fernández de la Pradilla, R.; Mallo, A.; Plumet, J.; Viso, A. Tetrahedron Lett. 1990, 31, 1475-1478.
28. (h) Fernández de la Pradilla, R.; Montero, C.; Viso, A. Chem. Commun. 1998, 409-410.
29. For reviews, see: (a) Satoh, T.; Yamakawa, K. Synlett 1992, 455-468. (b) Satoh, T. Chem. Rev. 1996, 96, 3303-3325. For a leading reference on the generation of oxiranyllithium reagents from sulfinyl oxiranes by ligand exchange, see; (c) Satoh, T.; Horiguchi, K. Tetrahedron Lett. 1995, 36, 8235-8238.
30. For reviews, see: (a) Satoh, T.; Yamakawa, K. Synlett 1992, 455-468. (b) Satoh, T. Chem. Rev. 1996, 96, 3303-3325. For a leading reference on the generation of oxiranyllithium reagents from sulfinyl oxiranes by ligand exchange, see; (c) Satoh, T.; Horiguchi, K. Tetrahedron Lett. 1995, 36, 8235-8238.
31. For reviews, see: (a) Satoh, T.; Yamakawa, K. Synlett 1992, 455-468. (b) Satoh, T. Chem. Rev. 1996, 96, 3303-3325. For a leading reference on the generation of oxiranyllithium reagents from sulfinyl oxiranes by ligand exchange, see; (c) Satoh, T.; Horiguchi, K. Tetrahedron Lett. 1995, 36, 8235-8238.
32. Satoh, T.; Oohara, T.; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130-3136.
33. (a) Tsuchihashi, G.; Mitamura, S.; Ogura, K. Tetrahedron Lett. 1974, 455-458. For the early reports on the direct Darzens condensation route to epoxy sulfoxides, see:
34. (b) Tsuchihashi, G.; Ogura, K. Bull. Chem. Soc. Jpn. 1972, 45, 2023-2027.
35. (c) Tavares, D. F.; Estep, R. E.; Blezard, M. Tetrahedron Lett. 1970, 2373-2376.
36. Evans, D. A.; Andrews, G. C. Acc. Chem. Res. 1974, 7, 147-155.
37. For a review on sulfinyl dienes, see: Aversa, M. C.; Baratucci, A.; Bonaccorsi, P.; Gianneto, P. Tetrahedron: Asymmetry 1997, 8, 1339-1367. See also ref 6b.
38. For selective epoxidations of 2-sulfonyl dienes, see: (a) Bäckvall, J.-E.; Ericsson, A. M.; Juntunen, S.; Nájera, C.; Yus, M. J. Org. Chem. 1993, 58, 5221-5225. (b) Bäckvall, J.-E.; Juntunen, S. J. Org. Chem. 1988, 53, 2398-2400. See also: (c) Hentemann, M. F.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 5615-5618.
39. For selective epoxidations of 2-sulfonyl dienes, see: (a) Bäckvall, J.-E.; Ericsson, A. M.; Juntunen, S.; Nájera, C.; Yus, M. J. Org. Chem. 1993, 58, 5221-5225. (b) Bäckvall, J.-E.; Juntunen, S. J. Org. Chem. 1988, 53, 2398-2400. See also: (c) Hentemann, M. F.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 5615-5618.
40. For selective epoxidations of 2-sulfonyl dienes, see: (a) Bäckvall, J.-E.; Ericsson, A. M.; Juntunen, S.; Nájera, C.; Yus, M. J. Org. Chem. 1993, 58, 5221-5225. (b) Bäckvall, J.-E.; Juntunen, S. J. Org. Chem. 1988, 53, 2398-2400. See also: (c) Hentemann, M. F.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 5615-5618.
41. For a synthesis of Hemibrevetoxin B based on sulfonyl oxiranes, see: (a) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. For related studies, see: (b) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158-8159. (c) Mori, Y.; Yaegashi, K.; Kazutaka, I.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605-2608. (d) Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917-12932. See also: (e) Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603-616. For an early report on the α-lithiation of sulfonyl oxiranes, see: (f) Ashwell, M.; Clegg, W.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. 1 1991, 897-908.
42. For a synthesis of Hemibrevetoxin B based on sulfonyl oxiranes, see: (a) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. For related studies, see: (b) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158-8159. (c) Mori, Y.; Yaegashi, K.; Kazutaka, I.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605-2608. (d) Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917-12932. See also: (e) Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603-616. For an early report on the α-lithiation of sulfonyl oxiranes, see: (f) Ashwell, M.; Clegg, W.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. 1 1991, 897-908.
43. For a synthesis of Hemibrevetoxin B based on sulfonyl oxiranes, see: (a) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. For related studies, see: (b) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158-8159. (c) Mori, Y.; Yaegashi, K.; Kazutaka, I.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605-2608. (d) Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917-12932. See also: (e) Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603-616. For an early report on the α-lithiation of sulfonyl oxiranes, see: (f) Ashwell, M.; Clegg, W.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. 1 1991, 897-908.
44. For a synthesis of Hemibrevetoxin B based on sulfonyl oxiranes, see: (a) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. For related studies, see: (b) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158-8159. (c) Mori, Y.; Yaegashi, K.; Kazutaka, I.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605-2608. (d) Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917-12932. See also: (e) Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603-616. For an early report on the α-lithiation of sulfonyl oxiranes, see: (f) Ashwell, M.; Clegg, W.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. 1 1991, 897-908.
45. For a synthesis of Hemibrevetoxin B based on sulfonyl oxiranes, see: (a) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. For related studies, see: (b) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158-8159. (c) Mori, Y.; Yaegashi, K.; Kazutaka, I.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605-2608. (d) Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917-12932. See also: (e) Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603-616. For an early report on the α-lithiation of sulfonyl oxiranes, see: (f) Ashwell, M.; Clegg, W.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. 1 1991, 897-908.
46. For a synthesis of Hemibrevetoxin B based on sulfonyl oxiranes, see: (a) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558. For related studies, see: (b) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158-8159. (c) Mori, Y.; Yaegashi, K.; Kazutaka, I.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605-2608. (d) Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917-12932. See also: (e) Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603-616. For an early report on the α-lithiation of sulfonyl oxiranes, see: (f) Ashwell, M.; Clegg, W.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. 1 1991, 897-908.
47. The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. H., Eds.; John Wiley & Sons: New York, 1988.
48. For the oxidation of sulfoxides with t-BuOOH, see: Breton, G. W.; Fields, J. D.; Kropp, P. J. Tetrahedron Lett. 1995, 36, 3825-3828.
49. For a preliminary communication, see: Fernández de la Pradilla, R.; Castro, S.; Manzano, P.; Priego, J.; Viso, A. J. Org. Chem. 1996, 61, 3586-3587.
50. Styryl sulfoxides 9a and, especially, 5a undergo conjugate addition with benzylamine much slower than related, less conjugated, substrates. See: (a)Pyne, S. G.; Griffith, R.; Edwards, M. Tetrahedron Lett. 1988, 29, 2089-2092. (b) Pyne, S. G.; Bloem, P.; Griffith, R. Tetrahedron 1989, 45, 7013-7022.
51. Styryl sulfoxides 9a and, especially, 5a undergo conjugate addition with benzylamine much slower than related, less conjugated, substrates. See: (a)Pyne, S. G.; Griffith, R.; Edwards, M. Tetrahedron Lett. 1988, 29, 2089-2092. (b) Pyne, S. G.; Bloem, P.; Griffith, R. Tetrahedron 1989, 45, 7013-7022.
52. (c) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093.
53. o-Nitrophenyl ethynyl sulfoxides display an enhanced reactivity with nucleophiles relative to their p-tolyl analogues. See: (a) Lee, A. W. M.; Chan, W. H. Topics Curr. Chem. 1997, 190, 103-129. (b) Lee, A. W. M.; Chan, W. H.; Tao, Y.; Lee, Y. K. J. Chem. Soc., Perkin Trans. 1 1994, 477-481.
54. o-Nitrophenyl ethynyl sulfoxides display an enhanced reactivity with nucleophiles relative to their p-tolyl analogues. See: (a) Lee, A. W. M.; Chan, W. H. Topics Curr. Chem. 1997, 190, 103-129. (b) Lee, A. W. M.; Chan, W. H.; Tao, Y.; Lee, Y. K. J. Chem. Soc., Perkin Trans. 1 1994, 477-481.
55. The use of tert-butyl sulfoxides allows for improved stereocontrol vs their p-tolyl analogues in some cases. For the preparation of optically pure tert-butyl sulfoxides, see: Khiar, N.; Fernández, I.; Alcudia, F. Tetrahedron Lett. 1994, 35, 5719-5722, and references therein.
56. This observation suggests that these vinyl oxiranes could be adequate substrates for π-allyl palladium chemistry. This possibility is being pursued in our laboratory.
57. For a review, see: Pasto, D. J.; Taylor, R. J. K. Org. React. 1991, 40, 91-155.
58. We have also reproduced the results of Tsuchihashi (ref 9a) on the treatment of E sulfoxide 5a with aqueous NBS and subsequent base-induced cyclization of the major bromohydrin to produce oxirane 8a; however, an attempt to apply this protocol to Z sulfoxide 9a led to a low conversion (ca. 25% after 4 h) of an equimolar mixture of bromohydrins.
59. For additions of malonate anions to 5a and 9a, see: (a) Tsuchihashi, G.; Mitamura, S.; Ogura, K. Tetrahedron Lett. 1976, 855-858. (b) See ref 17c.
60. For additions of malonate anions to 5a and 9a, see: (a) Tsuchihashi, G.; Mitamura, S.; Ogura, K. Tetrahedron Lett. 1976, 855-858. (b) See ref 17c.
61. These include the reversal of diastereoselectivity found for 1E sulfinyl dienes 31a and 31b and stannane 21 upon a change in the metal from Li to Na, as well as the stereochemical outcome of the epoxidation of related α-(1-hydroxyalkyl) and γ-oxygenated vinyl sulfoxides, see: Fernández de la Pradilla, R.; Manzano, P.; Priego, J.; Viso, A.; Martínez-Ripoll, M.; Rodríguez, A. Tetrahedron Lett. 1996, 37, 6793-6796.
62. Posner, G. H. Acc. Chem. Res. 1987, 20, 72-78, and references therein.
63. For a review, see: (a) Hoffman, R. W. Chem. Rev. 1989, 89, 1841-1860. See also: (b) Koizumi, T.; Arai, Y.; Takayama, H.; Kuriyama, K.; Shiro, M. Tetrahedron Lett. 1987, 28, 3689-3692.
64. For a review, see: (a) Hoffman, R. W. Chem. Rev. 1989, 89, 1841-1860. See also: (b) Koizumi, T.; Arai, Y.; Takayama, H.; Kuriyama, K.; Shiro, M. Tetrahedron Lett. 1987, 28, 3689-3692.
65. Watson, S. C.; Eastham, J. E. J. Organomet. Chem. 1967, 9, 165-168.
66. Andersen, K. K. Tetrahedron Lett. 1962, 93-96.
67. Kosugi, H.; Kitaoka, M.; Tagami, K.; Takahashi, A.; Uda, H. J. Org. Chem. 1987, 52, 1078-1082.
68. 2, 84%). See:
69. (b) McDougal, P. G.; Rico, J. G.; Oh, Y.-I.; Condon, B. D. J. Org. Chem. 1986, 51, 3388-3390.
70. (a) Posner, G. H.; Tang, P. W.; Mallamo, J. P. Tetrahedron Lett. 1978, 3995-3998.
71. (b) Okamura, H.; Mitsuhira, Y.; Miura, M.; Takei, H. Chem. Lett. 1978, 517-520.
72. Fawcett, J.; House, S.; Jenkins, P. R.; Lawrence, N. J.; Russell, D. R. J. Chem. Soc., Perkin Trans. 1 1993, 67-73.
73. Free radical addition of 2-methyl-2-propanethiol to 1-hexyne and oxidation with m-CPBA. See: Jacobs, T. L.; Illingworth, G. E. J. Org. Chem. 1963, 28, 2692.
74. 3N, THF. 4. n-BuCuCNLi, THF. Unpublished results from our laboratories. For related transformations, see ref 6d.
75. Truce, W. E.; Lusch, M. J. J. Org. Chem. 1978, 43, 2252-2258. See also ref 29.
76. Prepared from cyclohexanone and thiophenol and subsequent oxidation with m-CPBA. See: Labiad, B.; Villemin, D. Synthesis 1989, 143-144.
77. Yechezkel, T.; Ghera, E.; Ostercamp, D.; Hassner, A. J. Org. Chem. 1995, 60, 5135-5142. For the preparation of related enantiopure keto vinyl sulfoxides, see: Hulce, M.; Mallamo, J. P.; Frye, L. L.; Kogan, T. P.; Posner, G. H. Organic Syntheses; Wiley: New York, 1990; Coll. Vol. VII, pp 495-500.
78. Yechezkel, T.; Ghera, E.; Ostercamp, D.; Hassner, A. J. Org. Chem. 1995, 60, 5135-5142. For the preparation of related enantiopure keto vinyl sulfoxides, see: Hulce, M.; Mallamo, J. P.; Frye, L. L.; Kogan, T. P.; Posner, G. H. Organic Syntheses; Wiley: New York, 1990; Coll. Vol. VII, pp 495-500.