Enantioselective Diels-Alder reactions catalyzed by chiral magnesium Lewis acids prepared from hydroxysulfoxides

Tetrahedron Asymmetry

Volumn 7, Issue 9, 1996, Pages 2675-2686

  Ordonez M ^a   Guerrero De La Rosa, V ^a   Labastida, V ^a   Llera, J M ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

MAGNESIUM SALT; SULFOXIDE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030249750     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00344-8     Document Type: Article

References (52)

1. 1. a) Paquette, L.A. In Asymmetric Synthesis; Morrison, J.D. Ed.; Academic Press: New York, 1984; vol. 3B; pp. 455-499.
2. b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: New York, 1990; pp. 1-234.
3. c) Oppolzzer, W. In Comprehensive Organic Synthesis: Selectivity, Strategy & Efficiency in Modern Organic Chemistry; Trost, B.M.; Fleming, I. Eds.; Pergamon: Oxford, 1991, vol. 5; pp. 315-399.
4. 2. a) Narasaka, K. Synthesis 1991, 1-11.
5. b) Kagan, H.B. and Riant, O. Chem.Rev. 1992, 92, 1007-1019.
6. c) Kobayashi, S. Synlett. 1994, 689-701.
7. d) Oh, T. and Reilly, M. Org. Prep. and Proc. Int. 1994, 26, 129-158.
8. e)Togni, A. and Venanzi, L.M. Angew.Chem.Int.Ed.Engl. 1994, 33, 497-526.
9. 3. For recent reports see: a) Maruoka, K.; Oishi, M.; Shiohara, K. and Yamaraoto, H. Tetrahedron 1994, 50, 8983-8996.
10. b) Haase, C.; Sarko, Ch.R. and DiMare, M. J.Org.Chem. 1995, 60, 1777-1787.
11. c) Seebach, D.; Dahinden, R.; Marti, R.E.; Beck, A.K.; Plattner, D.A. and Kuhnle F.N.M J.Org.Chem. 1995, 60, 1788-1799.
12. d) Loh, T.P.; Wang, R.B. and Sim, K.Y. Tetrahedron Lett. 1996, 37, 2989-2992.
13. e) Hayashi, Y.; Rohde, J.J. and Corey, E.J. J.Am.Chem.Soc. 1996,118, 5502-5503.
14. 4. a) Corey, E.J.; Imai. N. and Zhang H.Y. J.Am.Chem.Soc. 1991, 113, 728-729.
15. b) Khiar, N.; Fernandez, I. and Alcudia, F. Tetrahedron Lett. 1993, 34, 123-126.
16. c) Ghosh, A.K.; Mathivanan, P. and Cappiello, J. Tetrahedron Lett. 1996, 37, 3815-3818.
17. d) Desimoni, G.; Faita, G. and Righetti, P.P. Tetrahedron Lett. 1996, 37, 3027-3030.
18. 5. a) Evans, D.A.; Miller, S.J. and Lectka, T. J.Am.Chem.Soc. 1993, 115, 6460-6461.
19. b) Evans, D.A.; Murry, J.A.; von Matt, P.; Norcross, R.D. and Miller, S.J. Angew.Chem.Int.Ed.Engl. 1995, 34, 798-800.
20. c) Davies, I.W.; Senanayake, C.H.; Larsen, R.D.; Verhoeven, T.R. and Reider, P.J. Tetrahedron Lett. 1996, 37, 1725-1726.
21. 6. a) Corey, E.J. and Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-6810.
22. b) Fujisawa, T.; Ichiyanagi, T. and Shimizu, M. Tetrahedron Lett. 1995, 36, 5031-5034.
23. 7. a) Kobayashi., S.; Hachiya, I.; Araki, M. and Ishitani, H. Tetrahedron Lett. 1993, 34, 3755-3758.
24. b) Kobayashi, S.; Hachiya, I.; Ishitani, H. and Araki, M. Tetrahedron Lett. 1993, 34, 4535-4538.
25. c) Kobayashi, S.; Araki, M. and Hachiya, I. J.Org.Chem. 1994, 59, 3758-3759.
26. d) Kobayashi, S.; Ishitani, H.; Hachiya, I. and Araki, M. Tetrahedron 1994, 50, 11623-11636.
27. e) Kobayashi, S.; Ishitani, H.; Araki, M. and Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328.
28. 8. Baldenius, K.U. and Kagan, H.B. Tetrahedron: Asymmetry 1990, 1, 597-610.
29. 9. a) Guerrero-de la Rosa, V.; Ordoñez, M., Alcudia, F. and Llera J.M. Tetrahedron Lett. 1995, 36, 4889-4892.
30. b) Llera, J.M.; Trujillo, M.; Blanco, M.E. and Alcudia, F. Tetrahedron:Asymmetry 1994, 5, 709-716.
31. 10. Andersen, K.K.; Gaffield, W.; Papanikolau, N.E.; Foley, J.W. and Perkins, R.I. J.Am.Chem.Soc. 1964, 86, 5637-5645.
32. 11. a) Klunder, J.M. and Sharpless, K.B. J.Org.Chem. 1987, 52, 2598-2602.
33. b) Lee, A.W.M.; Chan, W.H.; Tao, Y.; and Lee, Y.K. J.Chem.Soc.Perkin Trans I 1994, 477-481.
34. 12. Solladié, G.; Hutt, J. and Girardin, A. Synthesis 1987, 173-173.
35. 13. a) Llera, J.M.; Fernandez, I. and Alcudia, F. Tetrahedron Lett. 1991, 32, 7299-7302.
36. b) Fernandez, I.; Khiar, N.; Llera, J.M. and Alcudia, F. J.Org.Chem. 1992, 57, 6789-6796.
37. c) Guerrero-de la Rosa, V.; Ordoñez, M.; Llera, J.M. and Alcudia, F. Synthesis 1995, 761-762.
38. 14. a) Sakuraba, H. and Ushiki, S. Tetrahedron Lett. 1990, 31, 5349-5352.
39. b) Demailly, G.; Greck , Ch. and Solladié, G. Tetrahedron Lett. 1984, 25, 4113-4116.
40. 15. Handouchi, Ch. Tetrahedron Lett. 1992, 33, 1701-1704.
41. 16. a) Solladié, G.; Demailly, G. and Greck, Ch. Tetrahedron Lett. 1985, 26, 435-438.
42. b) Carreño, M.C.; Garcia-Ruano, J.L.; Martin, A.M.; Pedregal, C.; Rodriguez, J.H.; Rubio, A.; Sanchez, J. and Solladié, G. J.Org.Chem. 1990, 55, 2120-2128.
43. c) Alcudia, F.; Fernandez, I.; Llera, J.M. and Zorrilla, F An.Quim. 1988, 84C, 333-339.
44. 17. Annunziata, R.; Cinquini, M. and Cozzi, F. J.Chem.Soc.Perkin Trans I 1979, 1687-1690.
45. 18. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M. and Sugimori, J. J.Am.Chem.Soc. 1989, 111, 5340-5345.
46. 19. a) Whitesell, J.K. Acc.Chem.Res. 1985, 88, 280-284.
47. b)Evans, D.A.; Chapman, K.T. and Bisaha, J. J.Am.Chem.Soc. 1988, 110, 1238-1256 and references therein.
48. 20. Braun, M. Angew.Chem.Int.Ed.Engl. 1996, 35, 519-522.
49. 21. a) Brunner, H. Angew.Chem.Int.Ed.Engl. 1983, 22, 897-907.
50. b) Brunner, H. and Henrich, C. Tetrahedron: Asymmetry 1995, 6, 653-656.
51. 22. Jacobus, J. and Mislow, K. J.Am.Chem.Soc. 1967, 89, 5228-5234.
52. 23. Wright, J.; Drtina, G.J.; Roberts, R.A. and Paquette, L.A. J.Am.Chem.Soc. 1988, 110, 5806-5817.