1,3-Dipolar cycloaddition reactions of nitrones with alkyl vinyl ethers catalyzed by chiral oxazaborolidines

Tetrahedron

Volumn 53, Issue 34, 1997, Pages 11843-11852

  Seerden, Jean Paul G ^a   Boeren, Mike M M ^a   Scheeren, Hans W ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE; PYRROLIZIDINE ALKALOID;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYPERBARISM; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE;

EID: 0030877158     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00757-6     Document Type: Article

References (39)

1. Review : Frederickson, M. Tetrahedron 1997, 53, 403-425 and references cited therein.
2. a) Scarpati, R.; Sica, D.; Santacroce, C. Gazz. Chim. Ital. 1966, 96, 375-386;
3. b) Huisgen, R.; Grashey, R.; Seidl, H.; Hauck, H. Chem. Ber. 1968, 101, 2559-2563;
4. c) Keirs, D.; Moffat, D.; Overton, K.; Tomanek, R. J. Chem. Soc. Perkin Trans. 1 1991, 1041-1051;
5. d) Díaz-Ortiz, A.; Díez-Barra, E.; de la Hoz, A.; Prieto, P.; Moreno, A. J. Chem. Soc. Perkin Trans 1 1994, 3595-3598.
6. a) Paul, R.; Tchelitcheff, S. Bull. Soc. Chim. France 1967, 4179-4183;
7. b) Huisgen, R.; Grashey, R.; Seidl, H.; Hauck, H. Chem. Ber. 1968, 101, 2559-2567;
8. c) Dicken, C.M.; DeShong, P. J. Org. Chem. 1982, 47, 2047-2051; Dicken, C.M.; DeShong, P. ; Staib, R.R.; Freyer, A.J.; Weinreb, S.M. J. Org. Chem. 1982, 47, 4397;
9. c) Dicken, C.M.; DeShong, P. J. Org. Chem. 1982, 47, 2047-2051; Dicken, C.M.; DeShong, P. ; Staib, R.R.; Freyer, A.J.; Weinreb, S.M. J. Org. Chem. 1982, 47, 4397;
10. d) DeShong, P.; Leginus, J.M. J. Am. Chem. Soc. 1983, 105, 1686-1688; DeShong, P.; Dicken, C.M.; Leginus, J.M.; Whittle, R.R. J. Am. Chem. Soc. 1984, 106, 5598-5602;
11. d) DeShong, P.; Leginus, J.M. J. Am. Chem. Soc. 1983, 105, 1686-1688; DeShong, P.; Dicken, C.M.; Leginus, J.M.; Whittle, R.R. J. Am. Chem. Soc. 1984, 106, 5598-5602;
12. e) Iwashita, T.; Kusumi, T.; Kakisawa, H. Chem. Lett. 1979, 1337-1340; Iwashita, T.; Kusumi, T.; Kakisawa, H. J. Org. Chem. 1982, 47, 230-233;
13. e) Iwashita, T.; Kusumi, T.; Kakisawa, H. Chem. Lett. 1979, 1337-1340; Iwashita, T.; Kusumi, T.; Kakisawa, H. J. Org. Chem. 1982, 47, 230-233;
14. f) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S.V.; Merli, A. Tetrahedron : Asymmetry 1993, 4, 2131-2134;
15. g) Mukai, C.; Kim, I.J.; Cho, W.J.; Kido, M.; Hanaoka, M. J. Chem. Soc. Perkin Trans I, 1993, 2495-2503;
16. h) Murahashi, S.-I.; Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe. S. J. Org. Chem. 1990, 55, 1736-1744;
17. i) Joseph, R.; Sudalai, A.; Ravindranathan, T. Synlett 1995, 1177-1178.
18. a) Seerden, J.P.G.; Scholte op Reimer, A.W.A.; Scheeren, J.W. Tetrahedron Lett. 1994, 35, 4419-4422;
19. b) Seerden, J.P.G.; Kuypers, M.M.M.; Scheeren, J.W. Tetrahedron: Asymmetry 1995, 6, 1441-1450.
20. nitrone controlled 1,3-dipolar cycloadditions with electron-deficient dipolarophiles were reported: a) Gothelf, K.V.; Jørgensen, K.A. J. Org. Chem. 1994, 59, 5687-5691;
21. b) Gothelf, K.V.; Thomsen, I.; Jørgensen, K.A. J. Am. Chem. Soc. 1996, 118, 59-64;
22. c) Gothelf, K.V.; Hazell, R.G.; Jørgensen, K.A. J. Org. Chem. 1996, 61, 346-355;
23. d) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. Tetrahedron Lett. 1996, 37, 5947-5950;
24. d) Seebach, D.; Marti, R.E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740.
25. -1 less negative than ΔV‡ for the usual 1,4-cycloaddition (e.g. Diels-Alder) reaction. For examples see: a) Yoshimura, Y.; Osugi, J.; Nakahara, M. J. Am. Chem. Soc. 1983, 105, 5415-5418;
26. b) Ahn, C.; Kennington, Jr., J.W.; DeShong, P. J. Org. Chem. 1994, 59, 6282-6286. For references on the application of high pressure in organic synthesis see : Ciobanu, M.; Matsumoto, K. Liebigs Ann./Recueil 1997, 623-635; Matsumoto, K.; Archeson, R.M., Organic Synthesis at High Pressure, John Wiley & Sons, New York, 1991; Isaacs, N.S. Tetrahedron 1991, 47, 8463, and references cited therein.
27. b) Ahn, C.; Kennington, Jr., J.W.; DeShong, P. J. Org. Chem. 1994, 59, 6282-6286. For references on the application of high pressure in organic synthesis see : Ciobanu, M.; Matsumoto, K. Liebigs Ann./Recueil 1997, 623-635; Matsumoto, K.; Archeson, R.M., Organic Synthesis at High Pressure, John Wiley & Sons, New York, 1991; Isaacs, N.S. Tetrahedron 1991, 47, 8463, and references cited therein.
28. b) Ahn, C.; Kennington, Jr., J.W.; DeShong, P. J. Org. Chem. 1994, 59, 6282-6286. For references on the application of high pressure in organic synthesis see : Ciobanu, M.; Matsumoto, K. Liebigs Ann./Recueil 1997, 623-635; Matsumoto, K.; Archeson, R.M., Organic Synthesis at High Pressure, John Wiley & Sons, New York, 1991; Isaacs, N.S. Tetrahedron 1991, 47, 8463, and references cited therein.
29. b) Ahn, C.; Kennington, Jr., J.W.; DeShong, P. J. Org. Chem. 1994, 59, 6282-6286. For references on the application of high pressure in organic synthesis see : Ciobanu, M.; Matsumoto, K. Liebigs Ann./Recueil 1997, 623-635; Matsumoto, K.; Archeson, R.M., Organic Synthesis at High Pressure, John Wiley & Sons, New York, 1991; Isaacs, N.S. Tetrahedron 1991, 47, 8463, and references cited therein.
30. The pressure dependence of the enantioselectivity was assumed to originate from a difference in activation volume of the two possible diastereomeric transition state structures: Tietze, L.F.; Ott, C.; Gerke, K.; Buback, M. Angew. Chem. Int. Ed. Engl. 1993, 32, 1485-1486.
31. In the presence of 20 mol% of a chiral oxazaborolidine catalyst the reaction did not proceed at standard conditions in dichloromethane as solvent.
32. The related boron-phenyl substituted oxazaborolidines did not improve the enantioselectivity.
33. Takasu, M.; Yamamoto, H. Synlett 1990, 194.
34. Kiyooka, S.-i.; Kaneko, Y.; Kume, K. Tetrahedron Lett. 1992, 33, 4927.
35. Aben, R.W.M., Scheeren, J.W. J. Org. Chem. 1987, 52, 365.
36. Döpp, D.; Döpp, H. in "Houben-Weyl : Methoden der Organischen Chemie", vol E14b, Klamann, D.; Hagemann, H., Eds.; Georg Thieme Verlag, Stuttgart, 1990.
37. Murahashi, S.-I.; Shiota, T.; Imada, Y. Org. Synth. 1992, 70, 265-271; Murahashi, S.-I.; Mitsui, H.; Watanabe, T.; Zenki, S.-i. Tetrahedron Lett. 1983, 24, 1049-1052.
38. Murahashi, S.-I.; Shiota, T.; Imada, Y. Org. Synth. 1992, 70, 265-271; Murahashi, S.-I.; Mitsui, H.; Watanabe, T.; Zenki, S.-i. Tetrahedron Lett. 1983, 24, 1049-1052.
39. eAuflage, Georg Thieme Verlag, Stuttgart, 1974, pp. 223-233.