Electrophilic amination of 2-azadienes

Tetrahedron

Volumn 52, Issue 21, 1996, Pages 7585-7598

  Gouverneur, V ^a   Ghosez, L ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

2 azadiene; Diels Alder reaction; electrophilic amination; nitroso compound; amino acid

Indexed keywords

AMIDE;

CONFERENCE PAPER; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0029921035     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00268-2     Document Type: Conference Paper

References (41)

1. Ghosez, L.; Bayard, Ph.; Nshimyumukiza, P.; Gouverneur, V.; Sainte, F.; Beaudegnies, R.; Rivera, M.; Frisque-Hesbain, A.-M. and Wynants, C. Tetrahedron 1995, 51, 11021.
2. Ghosez, L.; Serckx-Poncin, B.; Rivera, M.; Bayard, P.; Sainte, F.; Demoulin, A.; Hesbain-Frisque, A.-M.; Mockel, A.; Munoz, L.; Bernard-Henriet, C. Lect Het. Chem. 1985, 8, 69; Bayard, P.; Ghosez, L. Tetrahedron Lett. 1988, 29, 6115; Bayard, P.; Sainte, F.; Beaudegnies, R.; Ghosez, L. Tetrahedron Lett. 1988, 3799; Rivera, M.; Lamy-Schelkens, H.; Sainte, F.; Mbiya, K.; Ghosez, L. Tetrahedron Lett. 1988, 4573; Lamy-Schelkens, H.; Giomi, D.; Ghosez, L.; Tetrahedron Lett. 1988, 5887; Lamy-Schelkens, H.; Ghosez, L. Tetrahedron Lett. 1989, 5891; Gouverneur, V.; Ghosez, L. Tetrahedron:Asymmetry 1991, 5349.
3. Ghosez, L.; Serckx-Poncin, B.; Rivera, M.; Bayard, P.; Sainte, F.; Demoulin, A.; Hesbain-Frisque, A.-M.; Mockel, A.; Munoz, L.; Bernard-Henriet, C. Lect Het. Chem. 1985, 8, 69; Bayard, P.; Ghosez, L. Tetrahedron Lett. 1988, 29, 6115; Bayard, P.; Sainte, F.; Beaudegnies, R.; Ghosez, L. Tetrahedron Lett. 1988, 3799; Rivera, M.; Lamy-Schelkens, H.; Sainte, F.; Mbiya, K.; Ghosez, L. Tetrahedron Lett. 1988, 4573; Lamy-Schelkens, H.; Giomi, D.; Ghosez, L.; Tetrahedron Lett. 1988, 5887; Lamy-Schelkens, H.; Ghosez, L. Tetrahedron Lett. 1989, 5891; Gouverneur, V.; Ghosez, L. Tetrahedron:Asymmetry 1991, 5349.
4. Ghosez, L.; Serckx-Poncin, B.; Rivera, M.; Bayard, P.; Sainte, F.; Demoulin, A.; Hesbain-Frisque, A.-M.; Mockel, A.; Munoz, L.; Bernard-Henriet, C. Lect Het. Chem. 1985, 8, 69; Bayard, P.; Ghosez, L. Tetrahedron Lett. 1988, 29, 6115; Bayard, P.; Sainte, F.; Beaudegnies, R.; Ghosez, L. Tetrahedron Lett. 1988, 3799; Rivera, M.; Lamy-Schelkens, H.; Sainte, F.; Mbiya, K.; Ghosez, L. Tetrahedron Lett. 1988, 4573; Lamy-Schelkens, H.; Giomi, D.; Ghosez, L.; Tetrahedron Lett. 1988, 5887; Lamy-Schelkens, H.; Ghosez, L. Tetrahedron Lett. 1989, 5891; Gouverneur, V.; Ghosez, L. Tetrahedron:Asymmetry 1991, 5349.
5. Ghosez, L.; Serckx-Poncin, B.; Rivera, M.; Bayard, P.; Sainte, F.; Demoulin, A.; Hesbain-Frisque, A.-M.; Mockel, A.; Munoz, L.; Bernard-Henriet, C. Lect Het. Chem. 1985, 8, 69; Bayard, P.; Ghosez, L. Tetrahedron Lett. 1988, 29, 6115; Bayard, P.; Sainte, F.; Beaudegnies, R.; Ghosez, L. Tetrahedron Lett. 1988, 3799; Rivera, M.; Lamy-Schelkens, H.; Sainte, F.; Mbiya, K.; Ghosez, L. Tetrahedron Lett. 1988, 4573; Lamy-Schelkens, H.; Giomi, D.; Ghosez, L.; Tetrahedron Lett. 1988, 5887; Lamy-Schelkens, H.; Ghosez, L. Tetrahedron Lett. 1989, 5891; Gouverneur, V.; Ghosez, L. Tetrahedron:Asymmetry 1991, 5349.
6. Ghosez, L.; Serckx-Poncin, B.; Rivera, M.; Bayard, P.; Sainte, F.; Demoulin, A.; Hesbain-Frisque, A.-M.; Mockel, A.; Munoz, L.; Bernard-Henriet, C. Lect Het. Chem. 1985, 8, 69; Bayard, P.; Ghosez, L. Tetrahedron Lett. 1988, 29, 6115; Bayard, P.; Sainte, F.; Beaudegnies, R.; Ghosez, L. Tetrahedron Lett. 1988, 3799; Rivera, M.; Lamy-Schelkens, H.; Sainte, F.; Mbiya, K.; Ghosez, L. Tetrahedron Lett. 1988, 4573; Lamy-Schelkens, H.; Giomi, D.; Ghosez, L.; Tetrahedron Lett. 1988, 5887; Lamy-Schelkens, H.; Ghosez, L. Tetrahedron Lett. 1989, 5891; Gouverneur, V.; Ghosez, L. Tetrahedron:Asymmetry 1991, 5349.
7. Ghosez, L.; Serckx-Poncin, B.; Rivera, M.; Bayard, P.; Sainte, F.; Demoulin, A.; Hesbain-Frisque, A.-M.; Mockel, A.; Munoz, L.; Bernard-Henriet, C. Lect Het. Chem. 1985, 8, 69; Bayard, P.; Ghosez, L. Tetrahedron Lett. 1988, 29, 6115; Bayard, P.; Sainte, F.; Beaudegnies, R.; Ghosez, L. Tetrahedron Lett. 1988, 3799; Rivera, M.; Lamy-Schelkens, H.; Sainte, F.; Mbiya, K.; Ghosez, L. Tetrahedron Lett. 1988, 4573; Lamy-Schelkens, H.; Giomi, D.; Ghosez, L.; Tetrahedron Lett. 1988, 5887; Lamy-Schelkens, H.; Ghosez, L. Tetrahedron Lett. 1989, 5891; Gouverneur, V.; Ghosez, L. Tetrahedron:Asymmetry 1991, 5349.
8. Ghosez, L.; Serckx-Poncin, B.; Rivera, M.; Bayard, P.; Sainte, F.; Demoulin, A.; Hesbain-Frisque, A.-M.; Mockel, A.; Munoz, L.; Bernard-Henriet, C. Lect Het. Chem. 1985, 8, 69; Bayard, P.; Ghosez, L. Tetrahedron Lett. 1988, 29, 6115; Bayard, P.; Sainte, F.; Beaudegnies, R.; Ghosez, L. Tetrahedron Lett. 1988, 3799; Rivera, M.; Lamy-Schelkens, H.; Sainte, F.; Mbiya, K.; Ghosez, L. Tetrahedron Lett. 1988, 4573; Lamy-Schelkens, H.; Giomi, D.; Ghosez, L.; Tetrahedron Lett. 1988, 5887; Lamy-Schelkens, H.; Ghosez, L. Tetrahedron Lett. 1989, 5891; Gouverneur, V.; Ghosez, L. Tetrahedron:Asymmetry 1991, 5349.
9. Boger, D.L.; Weinreb, S.N. "Hetero Diels-Alder Methodology in Organic Synthesis", Academic Press Inc. 1987 and references therein.
10. Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554; Kirby, G.W.; Nazeer, M. Tetrahedron Lett. 1988, 6173; Miller, A.; Mc Paterson, T.C.; Procter, G. Synlett 1989, 32; Braun, H.; Charles, R.; Kresze, G.; Sabuni, M.; Winkler, J. Liebigs Am. Chem. 1987, 1129; Feller, H.; Kresze, G.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1986, 69, 1137; Sabrini, M.; Kresze, G.; Braun, H. Tetrahedron Lett. 1979, 27, 3597; Felber, H.; Kresze, G.; Braun, H.; Vasella, A. Tetrahedron Lett. 1986, 27, 1895.
11. Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554; Kirby, G.W.; Nazeer, M. Tetrahedron Lett. 1988, 6173; Miller, A.; Mc Paterson, T.C.; Procter, G. Synlett 1989, 32; Braun, H.; Charles, R.; Kresze, G.; Sabuni, M.; Winkler, J. Liebigs Am. Chem. 1987, 1129; Feller, H.; Kresze, G.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1986, 69, 1137; Sabrini, M.; Kresze, G.; Braun, H. Tetrahedron Lett. 1979, 27, 3597; Felber, H.; Kresze, G.; Braun, H.; Vasella, A. Tetrahedron Lett. 1986, 27, 1895.
12. Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554; Kirby, G.W.; Nazeer, M. Tetrahedron Lett. 1988, 6173; Miller, A.; Mc Paterson, T.C.; Procter, G. Synlett 1989, 32; Braun, H.; Charles, R.; Kresze, G.; Sabuni, M.; Winkler, J. Liebigs Am. Chem. 1987, 1129; Feller, H.; Kresze, G.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1986, 69, 1137; Sabrini, M.; Kresze, G.; Braun, H. Tetrahedron Lett. 1979, 27, 3597; Felber, H.; Kresze, G.; Braun, H.; Vasella, A. Tetrahedron Lett. 1986, 27, 1895.
13. Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554; Kirby, G.W.; Nazeer, M. Tetrahedron Lett. 1988, 6173; Miller, A.; Mc Paterson, T.C.; Procter, G. Synlett 1989, 32; Braun, H.; Charles, R.; Kresze, G.; Sabuni, M.; Winkler, J. Liebigs Am. Chem. 1987, 1129; Feller, H.; Kresze, G.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1986, 69, 1137; Sabrini, M.; Kresze, G.; Braun, H. Tetrahedron Lett. 1979, 27, 3597; Felber, H.; Kresze, G.; Braun, H.; Vasella, A. Tetrahedron Lett. 1986, 27, 1895.
14. Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554; Kirby, G.W.; Nazeer, M. Tetrahedron Lett. 1988, 6173; Miller, A.; Mc Paterson, T.C.; Procter, G. Synlett 1989, 32; Braun, H.; Charles, R.; Kresze, G.; Sabuni, M.; Winkler, J. Liebigs Am. Chem. 1987, 1129; Feller, H.; Kresze, G.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1986, 69, 1137; Sabrini, M.; Kresze, G.; Braun, H. Tetrahedron Lett. 1979, 27, 3597; Felber, H.; Kresze, G.; Braun, H.; Vasella, A. Tetrahedron Lett. 1986, 27, 1895.
15. Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554; Kirby, G.W.; Nazeer, M. Tetrahedron Lett. 1988, 6173; Miller, A.; Mc Paterson, T.C.; Procter, G. Synlett 1989, 32; Braun, H.; Charles, R.; Kresze, G.; Sabuni, M.; Winkler, J. Liebigs Am. Chem. 1987, 1129; Feller, H.; Kresze, G.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1986, 69, 1137; Sabrini, M.; Kresze, G.; Braun, H. Tetrahedron Lett. 1979, 27, 3597; Felber, H.; Kresze, G.; Braun, H.; Vasella, A. Tetrahedron Lett. 1986, 27, 1895.
16. Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554; Kirby, G.W.; Nazeer, M. Tetrahedron Lett. 1988, 6173; Miller, A.; Mc Paterson, T.C.; Procter, G. Synlett 1989, 32; Braun, H.; Charles, R.; Kresze, G.; Sabuni, M.; Winkler, J. Liebigs Am. Chem. 1987, 1129; Feller, H.; Kresze, G.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1986, 69, 1137; Sabrini, M.; Kresze, G.; Braun, H. Tetrahedron Lett. 1979, 27, 3597; Felber, H.; Kresze, G.; Braun, H.; Vasella, A. Tetrahedron Lett. 1986, 27, 1895.
17. Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349.
18. Mc Clure, K.F.; Danishefsky, S.F. J. Org. Chem. 1991, 56, 850; Ried, W.; Reiher, U.; Bats, J.W. Helv. Chim. Acta 1987, 70, 1255; Taylor, E.C.; Mc Daniel, K.; Skotnicki, J.S. J. Org. Chem. 1984, 42, 2500.
19. Mc Clure, K.F.; Danishefsky, S.F. J. Org. Chem. 1991, 56, 850; Ried, W.; Reiher, U.; Bats, J.W. Helv. Chim. Acta 1987, 70, 1255; Taylor, E.C.; Mc Daniel, K.; Skotnicki, J.S. J. Org. Chem. 1984, 42, 2500.
20. Mc Clure, K.F.; Danishefsky, S.F. J. Org. Chem. 1991, 56, 850; Ried, W.; Reiher, U.; Bats, J.W. Helv. Chim. Acta 1987, 70, 1255; Taylor, E.C.; Mc Daniel, K.; Skotnicki, J.S. J. Org. Chem. 1984, 42, 2500.
21. We thank Dr J.-P. Declercq, J. Feneau-Dupont and Dr B. Tinant for the crystallographic study.
22. Kresze, G.; Weiss, M.M.; Dittel, W. Liebigs Ann. Chem. 1984, 203; Leonard, N.J.; Playtis, A.J.; Skoog, F.J.; Schmitz, R.Y. J. Am. Chem. Soc. 1971, 93, 3056; Leonard, N.J., Playtis, A.J. J. Chem. Soc. Chem. Commun. 1972, 133.
23. Kresze, G.; Weiss, M.M.; Dittel, W. Liebigs Ann. Chem. 1984, 203; Leonard, N.J.; Playtis, A.J.; Skoog, F.J.; Schmitz, R.Y. J. Am. Chem. Soc. 1971, 93, 3056; Leonard, N.J., Playtis, A.J. J. Chem. Soc. Chem. Commun. 1972, 133.
24. Kresze, G.; Weiss, M.M.; Dittel, W. Liebigs Ann. Chem. 1984, 203; Leonard, N.J.; Playtis, A.J.; Skoog, F.J.; Schmitz, R.Y. J. Am. Chem. Soc. 1971, 93, 3056; Leonard, N.J., Playtis, A.J. J. Chem. Soc. Chem. Commun. 1972, 133.
25. Kirby, G.W.; Mc Guigan, H.; Mac Kinnon, J.W.N.; Mc Lean, D.; Sharma, R.P. J. Chem. Soc. Perkin Trans 1 1985, 1437; Defoin, A.; Pires, J.; Streith, J. Synlett 1990, 111; Boger, D.L.; Patel, M. J. Org. Chem. 1984, 49, 4098; Boger, D.L.; Patel, M.; Takusagawa, F. J. Org. Chem. 1985, 50, 1911; Baldwin, J.E.; Otsuka, M.; Wallace, P.M. Tetrahedron 1986, 42, 3097; Keck, G.E. Tetrahedron Lett. 1978, 4767; Keck, G.E.; Nickell, D.G. J. Am. Chem. Soc. 1980, 102, 3632.
26. Kirby, G.W.; Mc Guigan, H.; Mac Kinnon, J.W.N.; Mc Lean, D.; Sharma, R.P. J. Chem. Soc. Perkin Trans 1 1985, 1437; Defoin, A.; Pires, J.; Streith, J. Synlett 1990, 111; Boger, D.L.; Patel, M. J. Org. Chem. 1984, 49, 4098; Boger, D.L.; Patel, M.; Takusagawa, F. J. Org. Chem. 1985, 50, 1911; Baldwin, J.E.; Otsuka, M.; Wallace, P.M. Tetrahedron 1986, 42, 3097; Keck, G.E. Tetrahedron Lett. 1978, 4767; Keck, G.E.; Nickell, D.G. J. Am. Chem. Soc. 1980, 102, 3632.
27. Kirby, G.W.; Mc Guigan, H.; Mac Kinnon, J.W.N.; Mc Lean, D.; Sharma, R.P. J. Chem. Soc. Perkin Trans 1 1985, 1437; Defoin, A.; Pires, J.; Streith, J. Synlett 1990, 111; Boger, D.L.; Patel, M. J. Org. Chem. 1984, 49, 4098; Boger, D.L.; Patel, M.; Takusagawa, F. J. Org. Chem. 1985, 50, 1911; Baldwin, J.E.; Otsuka, M.; Wallace, P.M. Tetrahedron 1986, 42, 3097; Keck, G.E. Tetrahedron Lett. 1978, 4767; Keck, G.E.; Nickell, D.G. J. Am. Chem. Soc. 1980, 102, 3632.
28. Kirby, G.W.; Mc Guigan, H.; Mac Kinnon, J.W.N.; Mc Lean, D.; Sharma, R.P. J. Chem. Soc. Perkin Trans 1 1985, 1437; Defoin, A.; Pires, J.; Streith, J. Synlett 1990, 111; Boger, D.L.; Patel, M. J. Org. Chem. 1984, 49, 4098; Boger, D.L.; Patel, M.; Takusagawa, F. J. Org. Chem. 1985, 50, 1911; Baldwin, J.E.; Otsuka, M.; Wallace, P.M. Tetrahedron 1986, 42, 3097; Keck, G.E. Tetrahedron Lett. 1978, 4767; Keck, G.E.; Nickell, D.G. J. Am. Chem. Soc. 1980, 102, 3632.
29. Kirby, G.W.; Mc Guigan, H.; Mac Kinnon, J.W.N.; Mc Lean, D.; Sharma, R.P. J. Chem. Soc. Perkin Trans 1 1985, 1437; Defoin, A.; Pires, J.; Streith, J. Synlett 1990, 111; Boger, D.L.; Patel, M. J. Org. Chem. 1984, 49, 4098; Boger, D.L.; Patel, M.; Takusagawa, F. J. Org. Chem. 1985, 50, 1911; Baldwin, J.E.; Otsuka, M.; Wallace, P.M. Tetrahedron 1986, 42, 3097; Keck, G.E. Tetrahedron Lett. 1978, 4767; Keck, G.E.; Nickell, D.G. J. Am. Chem. Soc. 1980, 102, 3632.
30. Kirby, G.W.; Mc Guigan, H.; Mac Kinnon, J.W.N.; Mc Lean, D.; Sharma, R.P. J. Chem. Soc. Perkin Trans 1 1985, 1437; Defoin, A.; Pires, J.; Streith, J. Synlett 1990, 111; Boger, D.L.; Patel, M. J. Org. Chem. 1984, 49, 4098; Boger, D.L.; Patel, M.; Takusagawa, F. J. Org. Chem. 1985, 50, 1911; Baldwin, J.E.; Otsuka, M.; Wallace, P.M. Tetrahedron 1986, 42, 3097; Keck, G.E. Tetrahedron Lett. 1978, 4767; Keck, G.E.; Nickell, D.G. J. Am. Chem. Soc. 1980, 102, 3632.
31. Kirby, G.W.; Mc Guigan, H.; Mac Kinnon, J.W.N.; Mc Lean, D.; Sharma, R.P. J. Chem. Soc. Perkin Trans 1 1985, 1437; Defoin, A.; Pires, J.; Streith, J. Synlett 1990, 111; Boger, D.L.; Patel, M. J. Org. Chem. 1984, 49, 4098; Boger, D.L.; Patel, M.; Takusagawa, F. J. Org. Chem. 1985, 50, 1911; Baldwin, J.E.; Otsuka, M.; Wallace, P.M. Tetrahedron 1986, 42, 3097; Keck, G.E. Tetrahedron Lett. 1978, 4767; Keck, G.E.; Nickell, D.G. J. Am. Chem. Soc. 1980, 102, 3632.
32. Boger, D.L.; Patel, M.; Takusagawa, F. J. Org.Chem 1985, 50, 1911.
33. Cicchi, S.; Goti, A.; Brandi, A.; Guarna, A., De Sarbo, F. Tetrahedron lett. 1990, 31, 3351; Baraldi, P.G.; Barco, A.; Benetti, S.; Mangredini, S.; Simoni, D. Synthesis 1987, 276.
34. Cicchi, S.; Goti, A.; Brandi, A.; Guarna, A., De Sarbo, F. Tetrahedron lett. 1990, 31, 3351; Baraldi, P.G.; Barco, A.; Benetti, S.; Mangredini, S.; Simoni, D. Synthesis 1987, 276.
35. Zenders, D.; Lotter, H.; Maigrot, N.; Maleyrat, J.P.; Welvart, Z. Nouveau Journal de Chimie 1984, 7, 747.
36. See for example Schollkopft, U.; Neubauer, H.J. Synthesis 1982, 861.
37. Kresze, G. Org. Prep. Proced. Int. 1987, 19, 329.
38. Porter, C.C.; Hellerman, L. J. Am. Chem. Soc. 1944, 66, 1652; Winterle, O.; Gregor, V.; Dubansky, A.; Seidl, V. Chem. Listy 1957, 51, 605.
39. Porter, C.C.; Hellerman, L. J. Am. Chem. Soc. 1944, 66, 1652; Winterle, O.; Gregor, V.; Dubansky, A.; Seidl, V. Chem. Listy 1957, 51, 605.
40. Boyland, E.; Nevy, R. J. Chem. Soc.(C) 1966, 354.
41. Stewart, A.O.; Brooks, D.W. J. Org. Chem. 1992, 57, 5020.