Diastereoselective formation of an [η4-(1Z)-sulfinyl diene]iron(0) tricarbonyl complex. Diastereoselective allylation of the derived iron dienal

Organometallics

Volumn 15, Issue 22, 1996, Pages 4672-4674

  Paley, Robert S ^a   Rubio, M Belén ^a   De La Pradilla, Roberto Fernández ^b   Dorado, Rocío ^b   Née Sood, Geeta Hundal ^c   Martínez Ripoll, Martín ^c  

^a SWARTHMORE COLLEGE   (United States)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^c INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008461752     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960654+     Document Type: Article

References (40)

1. For reviews, see: (a) The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M.; Eds.; Wiley: New York, 1988. (b) Posner, G. H. Acc. Chem. Res. 1987, 20, 72-87. (c) Solladié, G. Synthesis 1981, 185-196. (d) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968. (e) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
2. For reviews, see: (a) The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M.; Eds.; Wiley: New York, 1988. (b) Posner, G. H. Acc. Chem. Res. 1987, 20, 72-87. (c) Solladié, G. Synthesis 1981, 185-196. (d) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968. (e) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
3. For reviews, see: (a) The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M.; Eds.; Wiley: New York, 1988. (b) Posner, G. H. Acc. Chem. Res. 1987, 20, 72-87. (c) Solladié, G. Synthesis 1981, 185-196. (d) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968. (e) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
4. For reviews, see: (a) The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M.; Eds.; Wiley: New York, 1988. (b) Posner, G. H. Acc. Chem. Res. 1987, 20, 72-87. (c) Solladié, G. Synthesis 1981, 185-196. (d) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968. (e) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
5. For reviews, see: (a) The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M.; Eds.; Wiley: New York, 1988. (b) Posner, G. H. Acc. Chem. Res. 1987, 20, 72-87. (c) Solladié, G. Synthesis 1981, 185-196. (d) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968. (e) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
6. For examples of diastereoselective Diels-Alder reactions of unsaturated sulfoxides, see: (a) Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 115-122. (b) Arai, Y.; Matusi, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983-1985. (c) Carreño, M. C.; García-Ruano, J. L.; Urbano, A. Tetrahedron Lett. 1989, 30, 4003-4006.
7. For examples of diastereoselective Diels-Alder reactions of unsaturated sulfoxides, see: (a) Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 115-122. (b) Arai, Y.; Matusi, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983-1985. (c) Carreño, M. C.; García-Ruano, J. L.; Urbano, A. Tetrahedron Lett. 1989, 30, 4003-4006.
8. For examples of diastereoselective Diels-Alder reactions of unsaturated sulfoxides, see: (a) Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 115-122. (b) Arai, Y.; Matusi, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983-1985. (c) Carreño, M. C.; García-Ruano, J. L.; Urbano, A. Tetrahedron Lett. 1989, 30, 4003-4006.
9. For enantiospecific lactonizations of enantiopure vinylsulfoxides, see: (a) Marino, J. P.; Laborde, E.; Paley, R. S. J. Am. Chem. Soc. 1988, 110, 966-968. (b) Marino, J. P.; Perez, A. D. J. Am. Chem. Soc. 1984, 106, 7643-7644. (c) Marino, J. P.; Fernández de la Pradilla, R. Tetrahedron Lett. 1985, 25, 5381-5384. (d) Marino, J. P.; Bogdan, S.; Kimura, K. J. Am. Chem. Soc. 1992, 114, 5566-5572. (e) Marino, J. P. Pure Appl. Chem. 1993, 65, 667-674. (f) Burke, S. D.; Shankaran, K.; Helber, M. J. Tetrahedron Lett. 1991, 32, 4655-4658.
10. For enantiospecific lactonizations of enantiopure vinylsulfoxides, see: (a) Marino, J. P.; Laborde, E.; Paley, R. S. J. Am. Chem. Soc. 1988, 110, 966-968. (b) Marino, J. P.; Perez, A. D. J. Am. Chem. Soc. 1984, 106, 7643-7644. (c) Marino, J. P.; Fernández de la Pradilla, R. Tetrahedron Lett. 1985, 25, 5381-5384. (d) Marino, J. P.; Bogdan, S.; Kimura, K. J. Am. Chem. Soc. 1992, 114, 5566-5572. (e) Marino, J. P. Pure Appl. Chem. 1993, 65, 667-674. (f) Burke, S. D.; Shankaran, K.; Helber, M. J. Tetrahedron Lett. 1991, 32, 4655-4658.
11. For enantiospecific lactonizations of enantiopure vinylsulfoxides, see: (a) Marino, J. P.; Laborde, E.; Paley, R. S. J. Am. Chem. Soc. 1988, 110, 966-968. (b) Marino, J. P.; Perez, A. D. J. Am. Chem. Soc. 1984, 106, 7643-7644. (c) Marino, J. P.; Fernández de la Pradilla, R. Tetrahedron Lett. 1985, 25, 5381-5384. (d) Marino, J. P.; Bogdan, S.; Kimura, K. J. Am. Chem. Soc. 1992, 114, 5566-5572. (e) Marino, J. P. Pure Appl. Chem. 1993, 65, 667-674. (f) Burke, S. D.; Shankaran, K.; Helber, M. J. Tetrahedron Lett. 1991, 32, 4655-4658.
12. For enantiospecific lactonizations of enantiopure vinylsulfoxides, see: (a) Marino, J. P.; Laborde, E.; Paley, R. S. J. Am. Chem. Soc. 1988, 110, 966-968. (b) Marino, J. P.; Perez, A. D. J. Am. Chem. Soc. 1984, 106, 7643-7644. (c) Marino, J. P.; Fernández de la Pradilla, R. Tetrahedron Lett. 1985, 25, 5381-5384. (d) Marino, J. P.; Bogdan, S.; Kimura, K. J. Am. Chem. Soc. 1992, 114, 5566-5572. (e) Marino, J. P. Pure Appl. Chem. 1993, 65, 667-674. (f) Burke, S. D.; Shankaran, K.; Helber, M. J. Tetrahedron Lett. 1991, 32, 4655-4658.
13. For enantiospecific lactonizations of enantiopure vinylsulfoxides, see: (a) Marino, J. P.; Laborde, E.; Paley, R. S. J. Am. Chem. Soc. 1988, 110, 966-968. (b) Marino, J. P.; Perez, A. D. J. Am. Chem. Soc. 1984, 106, 7643-7644. (c) Marino, J. P.; Fernández de la Pradilla, R. Tetrahedron Lett. 1985, 25, 5381-5384. (d) Marino, J. P.; Bogdan, S.; Kimura, K. J. Am. Chem. Soc. 1992, 114, 5566-5572. (e) Marino, J. P. Pure Appl. Chem. 1993, 65, 667-674. (f) Burke, S. D.; Shankaran, K.; Helber, M. J. Tetrahedron Lett. 1991, 32, 4655-4658.
14. For enantiospecific lactonizations of enantiopure vinylsulfoxides, see: (a) Marino, J. P.; Laborde, E.; Paley, R. S. J. Am. Chem. Soc. 1988, 110, 966-968. (b) Marino, J. P.; Perez, A. D. J. Am. Chem. Soc. 1984, 106, 7643-7644. (c) Marino, J. P.; Fernández de la Pradilla, R. Tetrahedron Lett. 1985, 25, 5381-5384. (d) Marino, J. P.; Bogdan, S.; Kimura, K. J. Am. Chem. Soc. 1992, 114, 5566-5572. (e) Marino, J. P. Pure Appl. Chem. 1993, 65, 667-674. (f) Burke, S. D.; Shankaran, K.; Helber, M. J. Tetrahedron Lett. 1991, 32, 4655-4658.
15. (a) Solladié, G.; Lohse, O. J. Org. Chem. 1993, 58, 4555-4563.
16. (b) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreño, M. C.; García-Ruano, J. L. J. Org. Chem. 1991, 56, 2317 and references therein.
17. (a) Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153-156. Hiroi, K.; Onuma, H.; Arinaga, Y. Chem. Lett. 1995, 1099-1100.
18. (a) Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153-156. Hiroi, K.; Onuma, H.; Arinaga, Y. Chem. Lett. 1995, 1099-1100.
19. (b) Villar, J. M.; Delgado, A.; Llebaria, A.; Moretó, J. M. Tetrahedron: Asymmetry 1995, 6, 665-668.
20. (c) For a review of additions of organometallic reagents to sulfinyl cycloalkenones, see ref 1b.
21. 3 complexes have been reported: Ibbotson, A.; Reduto dos Reis, A. C.; Saberi, S. P.; Slawin, A. M. Z.; Thomas, S. E.; Tustin, G. J.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1 1992, 1251-1259. Pérez-Encabo, A.; Perrio, S.; Slawin, A. M. Z.; Thomas, S. E.; Wierzchleyski, A. T.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1 1994, 629-642.
22. 3 complexes have been reported: Ibbotson, A.; Reduto dos Reis, A. C.; Saberi, S. P.; Slawin, A. M. Z.; Thomas, S. E.; Tustin, G. J.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1 1992, 1251-1259. Pérez-Encabo, A.; Perrio, S.; Slawin, A. M. Z.; Thomas, S. E.; Wierzchleyski, A. T.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1 1994, 629-642.
23. (a) Paley, R. S.; de Dios, A.; Fernández de la Pradilla, R. Tetrahedron Lett. 1993, 34, 2429-2432.
24. (b) Paley, R. S.; Weers, H. L.; Fernández, P.; Fernández de la Pradilla, R.; Castro, S. Tetrahedron Lett. 1995, 36, 3605-3608.
25. Gaoni, Y. Tetrahedron Lett. 1977, 18, 4521-4524.
26. (a) Pearson, A. J. Iron Compounds in Organic Synthesis; Academic Press: San Diego, CA, 1994.
27. (b) Grée, R. Synthesis 1989, 341-355.
28. 5/NMO method used for complexations in this report: Shvo, Y.; Hazum, E. J. Chem. Soc., Chem. Commun. 1975, 829-830.
29. We are defining the diene plane, oriented as depicted in Figure 1, as the separation between the α (lower) face from the β (upper) face.
30. 3. This reagent was prepared according to a literature procedure: Alcock, N. W.; Danks, T. N.; Richards, C. J.; Thomas, S. E. Organometallics 1991, 10, 231-238.
31. For a review: Hoffman, R. W. Chem. Rev. 1989, 89, 1841-1860.
32. (a) For a recent examination of the mechanism of this process: Denmark, S. E.; Hosoi, S. J. Org. Chem. 1994, 59, 5133-5135.
33. (b) For an example of asymmetric allylborations of iron dienals, see: Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151-2152. Roush, W. R.; Park, J. C. Tetrahedron Lett. 1990, 31, 4707-4710.
34. (b) For an example of asymmetric allylborations of iron dienals, see: Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151-2152. Roush, W. R.; Park, J. C. Tetrahedron Lett. 1990, 31, 4707-4710.
35. Attempted conversion of the acetal to the aldehyde prior to complexation led to substantial isomerization about the Z double bond.
36. The atomic coordinates for this structure have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
37. 11
38. 3 complex derived from 3 prefers the s-cis conformation would seem to be strengthened.
39. Grée, R.; Laabassi, M.; Messet, P.; Carrié, R. Tetrahedron Lett. 1985, 26, 2317-2318.
40. For example, highly diastereoselective epoxidation of vinyl sulfoxides is possible: Fernández de la Pradilla, R.; Castro, S.; Manzano, P.; Priego, J.; Viso, A. J. Org. Chem. 1996, 61, 3586-3587.