Study of the reaction of imines derived from (R)-glyceraldehyde with Danishefsky's diene

Tetrahedron

Volumn 55, Issue 24, 1999, Pages 7601-7612

  Badorrey, Ramón ^a   Cativiela, Carlos ^a   Díaz de Villegas, María D ^a   Gálvez, José A ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

Alkaloids; Asymmetric synthesis; Diels Alder reactions; Nitrogen heterocycles

Indexed keywords

1,3 BUTADIENE; ACETONITRILE; GLYCERALDEHYDE; IMINE; IODIDE; MANNICH BASE; SOLVENT; ZINC;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DERIVATIZATION; DIASTEREOISOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033546447     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00377-4     Document Type: Article

References (45)

1. Strunz, G.M.; Findlay, J.A., in "The Alkaloids", Academic Press, New York, 1986, Vol. 26, pg. 89.
2. Numata, A.; Ibuka, T.; In "The Alkaloids", Academic Press, New York, 1987, Vol. 31, pg. 193.
3. Daly, J.W.; Garaffo, H.M.; Spande, T.F. in "The Alkaloids", Academic Press, San Diego, 1993, Vol 43, pg. 185.
4. Pinder, A.R. Nat. Prod. Rep. 1993, 10, 491.
5. Southon, I.W.; Buckingham, J., "Dictionary of Alkaloids", Chapman and Hall, London 1989.
6. Comins, D.L.; Joseph, S.P.; Goehring, R.R. J. Am. Chem. Soc. 1994, 116, 4719-4728.
7. Laschat, S. Liebigs Ann. 1997, 1-11.
8. Bailey, P.D.; Millwood, P.A.; Smith, P.D. Chem. Commun. 1998, 633-640.
9. Waldmann, H. Synthesis 1994, 535-551.
10. Tietze, L.F., Kettschau, G. Top. Curr. Chem. 1997, 189, 1-120.
11. 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, 786-788.
12. Abraham H.; Stella, L. Tetrahedron 1992, 48, 9707-9718.
13. MacFarlane, A.K.; Thomas, G.; Whiting, A. Tetrahedron Lett. 1993, 34, 2379-2382.
14. Bailey, P.D.; Londesbrough, D.J.; Hancox, T.C.; Heffernan, J.D.; Holmes, A.B. J. Chem. Soc., Chem. Commun. 1994, 2543-2344
15. Ager, D.; Cooper, N.; Cox, G.G.; Garro-Helion, F.; Harwood, L.M. Tetrahedron: Asymmetry 1996, 7, 2563-2566.
16. Midland, M.M.; Koops, R.W. J. Org. Chem. 1992, 57, 1158-1161 and references herein.
17. Ishimaru, K.; Yamamoto, Y.; Akiba, K. Tetrahedron 1997, 53, 5423-5432 and references herein.
18. Herczegh, P.; Kovacs, I.; Erdösi, G.; Varga, T.; Agócs, A.; Szilágyi, L.; Sztaricskai, F.; Bereceibar, A.; Lukacs, G.; Olesker, A. Pure Appl. Chem. 1997, 69, 519-524 and references herein.
19. Yu, L.; Li, J.; Ramirez, J.; Chem, D.; Wang, P.G. J. Org. Chem. 1997, 62, 903-907.
20. Kunz, H.; Pfrengle, W. Angew. Chem. Int. Ed. Engl. 1989, 28, 1067-1069.
21. Weymann, W.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160.
22. Larsen, S.D.; Grieco, P.A. J. Am. Chem. Soc. 1985, 107, 1768-1769.
23. Waldmann, H. Synlett 1995, 133-141. and references therein.
24. Devine, P.N.; Reilly, M.; Oh, T. Tetrahedron Lett. 1993, 34, 5827-5830.
25. Baldoli, C.; Del Buttero, P.; Di Ciolo, M.; Maiorana, S.; Papagni, A. Synlett 1996, 258-260.
26. Kündig, E.P.; Xu, L.H.; Romaens, P.; Bernardinelli, G. Synlett 1996, 270-272.
27. Hamada, T.; Zenkoh, T.; Sato, H.; Yonemitsu, O. Tetrahedron Lett. 1991, 32, 1649-1652.
28. Barluenga, J.; Aznar, F.; Ribas, C.; Valdés, C.; Fernandez, M.; Cabal, M.P.; Trujillo, J. Chem. Eur. J. 1996, 2, 805-811.
29. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. chem. Soc. 1994, 116, 10520-10524 and references therein.
30. Kobayashi, S.; Komiyama, S.; Ishitami, H. Angew. Chem. Int. Ed. 1998, 37, 979-989.
31. Cativiela, C.; Díaz-de-Villegas, M.D.; Gálvez, J.A. Tetrahedron Lett. 1995, 36, 2859-2860.
32. Cativiela, C.; Díaz-de-Villegas, M.D.; Gálvez, J.A. Tetrahedron: Asymmetry 1996, 7, 529-536.
33. Cativiela, C.; Díaz-de-Villegas, M.D.; Gálvez, J.A.; García, J.I. Tetrahedron 1996, 52, 9563-9574.
34. Badorrey, R.; Cativiela, C.; Díaz-de-Villegas, M.D.; Gálvez, J.A. Tetrahedron 1997, 53, 1411-1416.
35. Badorrey, R.; Cativiela, C.; Díaz-de-Villegas, M.D.; Gálvez, J.A. Synthesis 1997, 747-749.
36. Badorrey, R.; Cativiela, C.; Díaz-de-Villegas, M.D.; Gálvez, J.A. Tetrahedron Lett. 1997, 38, 2547-2550.
37. Waldmann, H.; Braun, M. J. Org. Chem. 1992, 57, 4444-4451.
38. Anh, N.T. Top. Curr. Chem. 1980, 88, 145.
39. Reetz, M.T. Acc. Chem. Res. 1993, 26, 462-468.
40. see ref 17 in Alvaro, G.; Savoia, D.; Valentinetti, M.R. Tetrahedron 1996, 52, 12571-12586.
41. Ishimaru, K; Watanabe, K.; Yamamoto, Y.; Akiba, K. Synlett 1994, 495-498.
42. Schmid, C.R.; Bryant, J.D.; Dowlatzedah, M.; Phillips, J.L.; Prather, D.E.; Schantz, R.D.; Sear, N.L.; Vianco, C.S. J. Org. Chem 1991, 56, 4056-4058.
43. Veith, V.; Leurs, S.; Jäger, V. Chem. Commun. 1996, 329-330.
44. Klein, M.; Wingen, V.; Buss, V. J. Am. Chem. Soc. 1987, 109, 6486-6492.
45. Hoffmann R.W. Chem. Rev. 1989, 89, 1841-1860.