A parallel combinatorial approach to locating homochiral Lewis acid catalysts for the asymmetric aza-Diels-Alder reaction of an imino dienophile

Tetrahedron Letters

Volumn 39, Issue 48, 1998, Pages 8905-8908

  Bromidge, Stephen ^a   Wilson, Paul C ^b   Whiting, Andrew ^b  

^a GLAXOSMITHKLINE   (United Kingdom)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALKADIENE; GLYOXYLIC ACID; IMINE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ENANTIOMER; GEL CHROMATOGRAPHY; METAL BINDING; STEREOCHEMISTRY; SYNTHESIS;

BETULACEAE;

EID: 0032569819     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01947-9     Document Type: Article

References (40)

1. 1. (a) Whiting, A.; "Advanced Asymmetric Synthesis", Stephenson, G.R.; ed., Chapt. 7, Blackie, London, 1996;
2. (b) Kagan, H.B.; Riant, O.; Chem. Rev. 1992, 92, 1007;
3. (c) Deloux, I.; Srebnik, M.; ibid 1993, 93, 763.
4. 2. (a) Waldman, H.; Synthesis 1994, 535;
5. (b) Narasaka, K.; ibid 1991, 1;
6. (c) Tomioka, K.; ibid 1990, 541.
7. 3. (a) Larsen, S.D.; Grieco, P.A.; J. Am. Chem. Soc. 1985, 107, 1768;
8. (b) Bailey, P.D.; Wilson, R.D.; Brown, G.R.; J. Chem. Soc., Perkin Trans. I 1991, 1337;
9. (c) Bailey, P.D.; Brown, G.R.; Kirber, F.; Reid, A.; Wilson, R.D.;Tetrahedron: Asymm. 1991, 2, 1263;
10. (d) Waldmann, H.; Braun, M.; L. Ann. Chem. 1991, 1045;
11. (e) Stella, L.; Abraham, H.; Feneau-Dupont, J.; Tinant, B.; Declercq, J. P.; Tetrahedron Lett. 1990, 31, 2603;
12. (f) Stella, I.; Abraham, H.; Tetrahedron 1992, 48, 9707;
13. (g) Grieco, P. A.; Parker, D. T.; Fobare, W. F.; Ruckle, R.; J. Am. Chem. Soc. 1987, 109, 5859;
14. (h) Grieco, P. A.; Bahsas, A.; J. Org. Chem. 1987, 52, 5746;
15. (i) Waldmann, H.; Angew. Chem., Int. Ed. Engl. 1988, 27, 274;
16. (j) Waldmann, H.; L. Am. Chem. 1989, 231;
17. (j) Waldmann, H.; Braun, M.; Drager, M.; Tetrahedron: Asymm. 1991, 2, 1231;
18. (k) Waldmann, H.; Braun, M.; Drager, M.; Angew. Chem., Int. Ed. Engl. 1990, 29, 1468;
19. (1) Waldmann, H.; Braun, M.; J. Org. Chem. 1992, 57, 4444;
20. (m) Pfrengle, W.; Kunz, H.; J. Org. Chem. 1989, 54, 4261;
21. (n) Maggini, M.; Prato, M.; Scorrano, G.;Tetrahedron Lett. 1990, 31, 6243;
22. (o) Hamley, P.; Helmchen, G.; Holmes, A. B.; Marshall, D. R.; Mackinnon, J.W. M.; Smith, D. F.; Ziller, J. W.; J. Chem. Soc., Chem. Commun. 1992, 786;
23. (p) McFarlane, A. K.; Thomas, G.; Whiting, A.; J. Chem. Soc. Perkin Trans. I , 1995, 2803;
24. (q) McFarlane, A.K.; Thomas; G.; Whiting, A.;Tetrahedron Lett. 1993, 34, 2379;
25. (p) Bailey, P. D.; Lundesbrough, D. J.; Hancox, T. C.; Heffernan, J. D.; Holmes, A. B.; Chem. Commun. 1994, 2543;
26. (q) Yu, L.; Li, J.; Ramirez, J.; Chen, D.; Wand, P.G. J. Org. Chem. 1997, 62, 903.
27. 4. (a) Hattori, K.; Yamamoto, H.; Tetrahedron 1993, 49, 1749;
28. (b) Idem, Synlett. 1993, 129.
29. 5. a) Ishitani, H.; Kobayashi, S.; Tetrahedron 1997, 53, 7357;
30. b) Kobayashi, S.; Komiyama, S.; Ishitani, H.; Angew. Chem., Int. Ed. Engl. 1998, 37, 979.
31. 6. Preliminary results were presented at two meetings: a) Pfizer Organic Chemistry Poster Symposium, London, December 1997;
32. b) 6th RSC-SCI Joint Meeting on Heterocyclic Meeting, Galway, Ireland, May 1998.
33. 7. Danishefsky, S.; Kitahara, T.; J. Am. Chem. Soc. 1974, 96, 7807.
34. 8. (a) Kobayashi, S.; Ishitani, H.; Nagayama, S.; Synthesis 1995, 1195;
35. (b) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Synlett. 1995, 975.
36. 9. (a) Danishefsky, S.; Kerwin Jr., J. F.; Tetrahedron Lett. 1982, 23, 3739;
37. (b) Jung, M.E.; Shishido, K.; Light, L.; Davis, L.; Tetrahedron Lett. 1981, 22, 4607.
38. 10. Burgess, K.; Lim, H-J.; Porte, A. M.; Sulikowski, G. A.; Angew. Chem., Int. Ed. Engl. 1996, 35, 220.
39. 11. Sarshar, S.; Mjalli, A.M.M.; "Annual Reports in Combinatorial Chemistry and Molecular Diversity", Moos, W.H.; Pavia, M.R.; Kay, B.K.; Ellington, A.D. eds., Vol. 1, p. 19, ESCOM, Leiden, Netherlands, 1997.
40. 4 requires C, 64.1; H, 5.8; H, 5.3; found C, 64.2; H, 5.7; N, 5.6 %.