(R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries in Diels-Alder reactions

Tetrahedron Asymmetry

Volumn 10, Issue 16, 1999, Pages 3123-3138

  Camps, Pelayo ^a   Font Bardia, Mercè ^b   Giménez, Sílvia ^a   Pérez, Francesc ^a   Solans, Xavier ^b   Soldevilla, Núria ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b Departament de Cristallografia   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; ACRYLIC ACID; ANTHRACENE; ANTHRACENE DERIVATIVE; CINNAMIC ACID; CROTONIC ACID DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; ISOPRENE; METHACRYLIC ACID; TITANIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL;

EID: 0033551926     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00267-0     Document Type: Article

References (45)

1. Camps, P.; Giménez, S.; Font-Bardia, M.; Solans, X. Tetrahedron: Asymmetry 1995, 6, 985-990.
2. Camps, P.; Giménez, S. Tetrahedron: Asymmetry 1995, 6, 991-1000.
3. Camps, P.; Giménez, S. Tetrahedron: Asymmetry 1996, 7, 1227-1234.
4. Camps, P.; Pérez, F.; Soldevilla, N. Tetrahedron: Asymmetry 1998, 9, 2065-2079.
5. Camps, P.; Pérez, F.; Soldevilla, N.; Borrego, M. A. Tetrahedron: Asymmetry 1999, 10, 493-509.
6. Camps, P.; Pérez, F.; Soldevilla, N. Tetrahedron: Asymmetry 1997, 8, 1877-1894.
7. Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257-3262.
8. Menezes, R. F.; Zezza, C. A.; Sheu, J.; Smith, M. B. Tetrahedron Lett. 1989, 30, 3295-3298.
9. Winterfeldt, E. Chem. Rev. 1993, 93, 827-843.
10. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1984, 106, 4261-4263.
11. Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3095-3098.
12. Evans, D. A.; Chapman, K. T.; Tan Hung, D.; Kawaguchi, A. T. Angew. Chem., Int. Ed. Engl. 1987, 26, 1184-1186.
13. Helmchen, G.; Ihrig, K.; Schindler, H. Tetrahedron Lett. 1987, 28, 183-186.
14. Pfrengle, W.; Kunz, H. J. Org. Chem. 1989, 54, 4261-4263.
15. Cativiela, C; López, P.; Mayoral, J. A. Tetrahedron: Asymmetry 1990, 1, 61-64.
16. Cativiela, C; López, P.; Mayoral, J. A. Tetrahedron: Asymmetry 1990, 1, 379-388.
17. Arai, Y.; Matsui, M.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 1233-1234.
18. Stella, L.; Abraham, H.; Feneau-Dupont, J.; Tinant, B.; Declercq, J. P. Tetrahedron Lett. 1990, 31, 2603-2606.
19. Miyaji, K.; Ohara, Y.; Takahashi, Y.; Tsuruda, T.; Arai, K. Tetrahedron Lett. 1991, 32, 4557-4560.
20. Cativiela, C.; Mayoral, J. A.; Avenoza, A.; Peregrina, J. M.; Lahoz, F. J.; Gimeno, S. J. Org. Chem. 1992, 57, 4664-4669.
21. Nouguier, R.; Gras, J. L.; Giraud, B.; Virgili, A. Tetrahedron 1992, 48, 6245-6252.
22. Kim, B. H.; Curran, D. P. Tetrahedron 1993, 49, 293-318.
23. Cativiela, C.; Avenoza, A.; París, M.; Peregrina, J. M. J. Org. Chem. 1994, 59, 7774-7778.
24. Corey, E. J.; Loh, T.-P. J. Am. Chem. Soc. 1991, 113, 8966-8967.
25. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019.
26. Seerden, J.-P. G.; Scheeren, H. W. Tetrahedron Lett. 1993, 34, 2669-2672.
27. Corey, E. J.; Guzmán-Pérez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611-3612.
28. Corey, E. J.; Sarshar, S.; Lee, D.-H. J. Am. Chem. Soc. 1994, 116, 12089-12090.
29. Aggarwal, V. K.; Anderson, E.; Giles, R.; Zaparucha, A. Tetrahedron: Asymmetry 1995, 6, 1301-1306.
30. Corey, E. J.; Letavic, M. A. J. Am. Chem. Soc. 1995, 117, 9616-9617.
31. Evans, D. A.; Shaughnessy, E. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 3193-3194.
32. Otto, S.; Boccaletti, G.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1998, 120, 4238-4239.
33. Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920-6930.
34. Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S.; Collins, S. Organometallics 1998, 17, 914-925.
35. Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253-6256.
36. An improved procedure for the large-scale preparation of (R)- and (S)-1 has been developed: Camps, P.; Pérez, F.; Soldevilla, N. Tetrahedron Lett. 1999, 40, in press.
37. Hart, H. Tetrahedron 1986, 42, 1641-1654.
38. Hu, Y.; Yamada, K. A.; Chalmers, D. K.; Annavajjula, D. P.; Covey, D. F. J. Am. Chem. Soc. 1996, 118, 4550-4559.
39. Berson, J. A.; Bergman, R. G.; Hammons, J. H.; McRowe, A. W. J. Am. Chem. Soc. 1967, 89, 2581-2589.
40. Brower, M.; Stothers, J. B.; Tan, C. T. Org. Magn. Reson. 1977, 9, 360-366.
41. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473.
42. Sheldrick, G. M. SHELX-93, Program for Crystal Structure Determinations; University of Göttingen: Germany, 1994.
43. International Tables of X-Ray Crystallography; Kynock Press: Birmingham, 1974; vol IV, pp. 99-100 and 149.
44. Flack, H. D. Acta Crystallogr. 1983, A39, 876-881.
45. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application, supplying a full journal reference, to: The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: 44 +(1223) 336-033; e-mail: deposit@chemcrys.cam.ac.uk).