Enantioselective synthesis of 4-aminocyclopent-2-ene-1-one from tricyclo[5.2.1.02,6]decenyl enaminones

Tetrahedron Letters

Volumn 39, Issue 11, 1998, Pages 1429-1432

  Ramesh, Namakkal G ^a   Klunder, Antonius J H ^a   Zwanenburg, Binne ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENONE DERIVATIVE; ENAMINE;

ARTICLE; COVALENT BOND; DIASTEREOISOMER; ENANTIOMER; SYNTHESIS;

EID: 0032510372     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10820-6     Document Type: Article

References (37)

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28. 11. In our laboratory, this methodology has been successfully applied for the synthesis of a variety of cyclopentanoid natural products. For an illustrative example, see ref. 1.
29. 12. Comins, D.L.; LaMunyon, D.H. Tetrahedron Lett., 1989, 30, 5053-5056; Michael, J.P.; Parsons, A.S.; Hunter, R. Tetrahedron Lett., 1989, 30, 4879-4880; Imhof, R.; Kyburz, E.; Daly, J.J. J. Med. Chem., 1984, 27, 165-175; Nikiforov, T.; Stanchev, S.; Milenkov, B.; Dimitrov, V. Heterocycles, 1980, 24, 1825-1829; Schuda, P.F.; Ebner, C.B.; Morgan, T.M. Tetrahedron Lett., 1986, 27, 2567-2570; Weselowsky, V.W.; Moiseenkov, A.M. Synthesis, 1974, 58-59; Borch, R.F.; Bernstein, M.D.; Durst, H.D. J. Am. Che. Soc., 1971, 93, 2897-2904.
30. 12. Comins, D.L.; LaMunyon, D.H. Tetrahedron Lett., 1989, 30, 5053-5056; Michael, J.P.; Parsons, A.S.; Hunter, R. Tetrahedron Lett., 1989, 30, 4879-4880; Imhof, R.; Kyburz, E.; Daly, J.J. J. Med. Chem., 1984, 27, 165-175; Nikiforov, T.; Stanchev, S.; Milenkov, B.; Dimitrov, V. Heterocycles, 1980, 24, 1825-1829; Schuda, P.F.; Ebner, C.B.; Morgan, T.M. Tetrahedron Lett., 1986, 27, 2567-2570; Weselowsky, V.W.; Moiseenkov, A.M. Synthesis, 1974, 58-59; Borch, R.F.; Bernstein, M.D.; Durst, H.D. J. Am. Che. Soc., 1971, 93, 2897-2904.
31. 12. Comins, D.L.; LaMunyon, D.H. Tetrahedron Lett., 1989, 30, 5053-5056; Michael, J.P.; Parsons, A.S.; Hunter, R. Tetrahedron Lett., 1989, 30, 4879-4880; Imhof, R.; Kyburz, E.; Daly, J.J. J. Med. Chem., 1984, 27, 165-175; Nikiforov, T.; Stanchev, S.; Milenkov, B.; Dimitrov, V. Heterocycles, 1980, 24, 1825-1829; Schuda, P.F.; Ebner, C.B.; Morgan, T.M. Tetrahedron Lett., 1986, 27, 2567-2570; Weselowsky, V.W.; Moiseenkov, A.M. Synthesis, 1974, 58-59; Borch, R.F.; Bernstein, M.D.; Durst, H.D. J. Am. Che. Soc., 1971, 93, 2897-2904.
32. 12. Comins, D.L.; LaMunyon, D.H. Tetrahedron Lett., 1989, 30, 5053-5056; Michael, J.P.; Parsons, A.S.; Hunter, R. Tetrahedron Lett., 1989, 30, 4879-4880; Imhof, R.; Kyburz, E.; Daly, J.J. J. Med. Chem., 1984, 27, 165-175; Nikiforov, T.; Stanchev, S.; Milenkov, B.; Dimitrov, V. Heterocycles, 1980, 24, 1825-1829; Schuda, P.F.; Ebner, C.B.; Morgan, T.M. Tetrahedron Lett., 1986, 27, 2567-2570; Weselowsky, V.W.; Moiseenkov, A.M. Synthesis, 1974, 58-59; Borch, R.F.; Bernstein, M.D.; Durst, H.D. J. Am. Che. Soc., 1971, 93, 2897-2904.
33. 12. Comins, D.L.; LaMunyon, D.H. Tetrahedron Lett., 1989, 30, 5053-5056; Michael, J.P.; Parsons, A.S.; Hunter, R. Tetrahedron Lett., 1989, 30, 4879-4880; Imhof, R.; Kyburz, E.; Daly, J.J. J. Med. Chem., 1984, 27, 165-175; Nikiforov, T.; Stanchev, S.; Milenkov, B.; Dimitrov, V. Heterocycles, 1980, 24, 1825-1829; Schuda, P.F.; Ebner, C.B.; Morgan, T.M. Tetrahedron Lett., 1986, 27, 2567-2570; Weselowsky, V.W.; Moiseenkov, A.M. Synthesis, 1974, 58-59; Borch, R.F.; Bernstein, M.D.; Durst, H.D. J. Am. Che. Soc., 1971, 93, 2897-2904.
34. 12. Comins, D.L.; LaMunyon, D.H. Tetrahedron Lett., 1989, 30, 5053-5056; Michael, J.P.; Parsons, A.S.; Hunter, R. Tetrahedron Lett., 1989, 30, 4879-4880; Imhof, R.; Kyburz, E.; Daly, J.J. J. Med. Chem., 1984, 27, 165-175; Nikiforov, T.; Stanchev, S.; Milenkov, B.; Dimitrov, V. Heterocycles, 1980, 24, 1825-1829; Schuda, P.F.; Ebner, C.B.; Morgan, T.M. Tetrahedron Lett., 1986, 27, 2567-2570; Weselowsky, V.W.; Moiseenkov, A.M. Synthesis, 1974, 58-59; Borch, R.F.; Bernstein, M.D.; Durst, H.D. J. Am. Che. Soc., 1971, 93, 2897-2904.
35. 12. Comins, D.L.; LaMunyon, D.H. Tetrahedron Lett., 1989, 30, 5053-5056; Michael, J.P.; Parsons, A.S.; Hunter, R. Tetrahedron Lett., 1989, 30, 4879-4880; Imhof, R.; Kyburz, E.; Daly, J.J. J. Med. Chem., 1984, 27, 165-175; Nikiforov, T.; Stanchev, S.; Milenkov, B.; Dimitrov, V. Heterocycles, 1980, 24, 1825-1829; Schuda, P.F.; Ebner, C.B.; Morgan, T.M. Tetrahedron Lett., 1986, 27, 2567-2570; Weselowsky, V.W.; Moiseenkov, A.M. Synthesis, 1974, 58-59; Borch, R.F.; Bernstein, M.D.; Durst, H.D. J. Am. Che. Soc., 1971, 93, 2897-2904.
36. 2. The organic layer was then dried, concentrated and purified by column chromatography to yield a diastereomeric mixture of β-amino ketones 9 and 10.
37. 3 and integrating the separation of the signal due to the β-olefinic proton.