Highly stereoselective synthesis of functionalized β,β-di- and trisubstituted vinylic sulfoxides by cu-catalyzed conjugate addition of organozinc reagents

Journal of Organic Chemistry

Volumn 69, Issue 24, 2004, Pages 8387-8393

  Maezaki, Naoyoshi ^a   Sawamoto, Hiroaki ^a   Suzuki, Tomoko ^a   Yoshigami, Ryoko ^a   Tanaka, Tetsuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; NEGATIVE IONS; SYNTHESIS (CHEMICAL);

CARBANIONS; ELECTROPHILES; MICHAEL ADDITION;

ZINC;

COPPER; SULFOXIDE; VINYL DERIVATIVE; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHIRALITY; CONJUGATE; DERIVATIZATION; MICHAEL ADDITION; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 9344226809     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048747l     Document Type: Article

References (51)

1. For reviews of sulfoxides, see: (a) Fernández, I.; Khiar, N. Chem. Rev. 2003, 103, 3651-3705.
2. (b) Procter, D. J. J. Chem. Soc., Perkin Trans. 1 2001, 335-354.
3. (c) Procter, D. J. J. Chem. Soc., Perkin Trans. 1 2000, 835-871.
4. (d) Carretero, J. C.; Arrayás, R. G.; Buezo, N. D.; Garrido, J. L.; Alonso, I.; Adrio, J. Phosphrous, Sulfur Silicon Relat. Elem. 1999, 153-154, 259-273.
5. (e) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P. Tetrahedron: Asymmetry 1997, 8, 1339-1367.
6. (f) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
7. (g) Marino, J. P. Pure Appl. Chem. 1993, 65, 667-674.
8. (h) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-998.
9. (i) Koizumi, T. Phosphrous, Sulfur Silicon Relat. Elem. 1991, 58, 111-127.
10. For geometric selective synthesis of β-monosubstituted vinylic sulfoxides, see: (a) van Steenis, J. H.; van Es, J. J. G. S.; van der Gen, A. Eur. J. Org. Chem. 2000, 65, 2787-2793.
11. (b) Segorbe, M. M.; Adrio, J.; Carretero, J. C. Tetrahedron Lett. 2000, 41, 1983-1986.
12. (c) Mikolajczyk, M.; Perlikowska, W.; Omelañczuk, J.; Cristau, H.-J.; Perraud-Darcy, A. J. Org. Chem. 1998, 63, 9716-9722.
13. (d) Kosugi, H.; Kitaoka, M.; Tagami, K.; Takahashi, A.; Uda, H. J. Org. Chem. 1987, 52, 1078-1082.
14. (e) Kosugi, H.; Kitaoka, M.; Tagami, K.; Uda, H. Chem. Lett. 1985, 805-808.
15. (f) Posner, G. H.; Tang, P.-W. J. Org. Chem. 1978, 43, 4131-4136.
16. (g) Abbott, D. J.; Colonna, S.; Stirling, J. M. J. Chem. Soc. D 1971, 471.
17. For geometric selective synthesis of β,β-disubstituted vinylic sulfoxides, see: (a) Alonso, I.; Carretero, J. C. J. Org. Chem. 2001, 66, 4453-4456.
18. (b) Ruano, J. L. G.; de Diego, S. A. A.; Blanco, D.; Castro, A. M. M.; Martin, M. R.; Ramos, J. H. R. Org. Lett. 2001, 3, 3173-3176.
19. (c) Ruano, J. L. G.; Gamboa, A. E.; Castro, A. M. M.; Rodríguez, J. H.; López-Solera, M. I. J. Org. Chem. 1998, 63, 3324-3332 and ref 2d.
20. (a) 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.; de la Pradilla, R. F.; Castro, S.; Dorado, R.; Morente, M. J. Org. Chem. 1997, 62, 6326-6343.
21. (b) Paley, R. S.; Weers, H. L.; Fernández, P.; de la Pradilla, R. F.; Castro, S. Tetrahedron Lett. 1995, 36, 3605-3608.
22. (c) Kosugi, H.; Miura, Y.; Kanna, H.; Uda, H. Tetrahedron: Asymmetry 1993, 4, 1409-1412.
23. (d) Truce, W. E.; Lusch, M. J. J. Org. Chem. 1978, 43, 2252-2258.
24. (e) Vermeer, P.; Meijer, J.; Eylander, M. C. Recl. Trav. Chim. Pays-Bas 1974, 93, 240-241 and ref 2d.
25. Maezaki, N.; Sawamoto, H.; Yoshigami, R.; Suzuki, T.; Tanaka, T. Org. Lett. 2003, 5, 1345-1347.
26. The assignment of the olefin geometry was conducted by NOE experiment between the olefinic proton and the cis-substituent. High optical purity of 4a was confirmed by chiral HPLC (Daisel Chiralcel OB) in comparison with the racemic sample.
27. Houpis, I. N.; Lee, J. Tetrahedron 2000, 56, 817-846.
28. (a) Stadtmüller, H.; Vaupel, A.; Tucker, C. E.; Stüdemann, T.; Knochel, P. Chem.-Eur. J. 1996, 2, 1204-1220.
29. (b) Rozema, M. J.; Eisenberg, C.; Lutjens, H.; Ostwald, R.; Belyk, K.; Knochel, P. Tetrahedron Lett. 1993, 34, 3115-3118.
30. (a) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414-4435.
31. (b) Nakamura, M.; Nakamura, E. J. Synth. Org. Chem. Jpn. 1998, 56, 632-644 and references therein.
32. Posner and Okamura independently reported that α-sulfinyl vinyllithium generated by α-deprotonation of (Z)-vinylic sulfoxide immediately isomerizes to thermodynamically stable (E)-isomer (Posner, G. H.; Tang, P.-W.; Mallamo, J. P. Tetrahedron Lett. 1978, 3995-3998. Okamura, H.; Mitsuhira, Y.; Miura, M.; Takei, H. Chem. Lett. 1978, 517-520). In sharp contrast, no E/Z-isomerization was observed in α-sulfinyl vinylic carbanion generated by conjugate addition of organocopper reagents to 1-alkynyl sulfoxides (ref 4). The difference presumably arises from the ionic nature of the carbon-lithium bond as compared with the carbon-copper bond. With these facts in mind, we speculate that the organomagnesium intermediate in the reaction of Scheme 1 is geometrically more unstable due to its ionic nature than the corresponding organozinc intermediate in carbozincation, thereby suffering from E/Z-isomerization.
33. Posner and Okamura independently reported that α-sulfinyl vinyllithium generated by α-deprotonation of (Z)-vinylic sulfoxide immediately isomerizes to thermodynamically stable (E)-isomer (Posner, G. H.; Tang, P.-W.; Mallamo, J. P. Tetrahedron Lett. 1978, 3995-3998. Okamura, H.; Mitsuhira, Y.; Miura, M.; Takei, H. Chem. Lett. 1978, 517-520). In sharp contrast, no E/Z-isomerization was observed in α-sulfinyl vinylic carbanion generated by conjugate addition of organocopper reagents to 1-alkynyl sulfoxides (ref 4). The difference presumably arises from the ionic nature of the carbon-lithium bond as compared with the carbon-copper bond. With these facts in mind, we speculate that the organomagnesium intermediate in the reaction of Scheme 1 is geometrically more unstable due to its ionic nature than the corresponding organozinc intermediate in carbozincation, thereby suffering from E/Z-isomerization.
34. (a) Xu, Q.; Huang, X. Tetrahedron Lett. 2004, 45, 5657-5660.
35. (b) Satoh, T.; Yoshida, M.; Takahashi, Y.; Ota, H. Tetrahedron: Asymmetry 2002, 14, 281-288.
36. (c) Arroyo, Y.; Carreño, M. C.; Ruano, J. L. G.; Amo, J. F. R.; Santos, M.; Tejedor, M. A. S. Tetrahedron: Asymmetry 2000, 11, 1183-1191 and ref 4a,b.
37. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390-2392.
38. (a) Iwata, C.; Maezaki, N.; Hattori, K.; Fujita, M.; Moritani, Y.; Takemoto, Y.; Tanaka, T.; Imanishi, T. Chem. Pharm. Bull. 1993, 41, 339-345.
39. (b) Iwata, C.; Fujita, M.; Kuroki, T.; Hattori, K.; Uchida, S.; Imanishi, T. Chem. Pharm. Bull. 1988, 36, 3257-3263.
40. (c) Iwata, C.; Hattori, K.; Kuroki, T.; Uchida, S.; Imanishi, T. Chem. Pharm. Bull. 1988, 36, 2909-2917.
41. (d) Iwata, C.; Moritani, Y.; Sugiyama, K.; Fujita, M.; Imanishi, T. Tetrahedron Lett. 1987, 28, 2255-2258.
42. (e) Iwata, C.; Fujita, M.; Hattori, K.; Uchida, S.; Imanishi, T. Tetrahedron Lett. 1985, 26, 2221-2224.
43. (f) Iwata, C.; Hattori, K.; Uchida, S.; Imanishi, T. Tetrahedron Lett. 1984, 25, 2995-2998.
44. The product 9f was a 1.8:1 mixture of two isomers, but the structures were not determined.
45. Akiyama, T.; Yasusa, T.; Ishikawa, K.; Ozaki, S. Tetrahedron Lett. 1994, 35, 8401-8404.
46. Knochel, P.; Rozema, M. J.; Tucker, C. E. In Organocopper Reagents: A Practical Approach; Taylor, R. J. K., Ed.; Harwood, L. M., Moody, C. J., Series Eds.; Oxford University Press: Oxford, 1994; Chapter 4, pp 85-104.
47. Cinquini, M.; Colonna, S.; Cozzi, F.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 1 1976, 2061-2067.
48. Maezaki, N.; Yoshigami, R.; Maeda, J.; Tanaka, T. Org. Lett. 2001, 3, 3627-3629.
49. Macours, P.; Braekman, J. C.; Daloze, D. Tetrahedron 1995, 51, 1415-1428.
50. Louis, C.; Mill, S.; Mancuso, V.; Hootele, C. Can. J. Chem. 1994, 72, 1347-1350.
51. Maezaki, N.; Izumi, M.; Yuyama, S.; Sawamoto, H.; Iwata, C.; Tanaka, T. Tetrahedron 2000, 56, 7927-7945.