A heterocycle-forming double Michael reaction. [5 + 1] Annulation route to highly substituted and functionalized piperidines

Organic Letters

Volumn 3, Issue 18, 2001, Pages 2911-2914

  Hughes Jr , Freddie ^a   Grossman, Robert B ^a  

^a UNIVERSITY OF KENTUCKY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIETHYL AMINOMALONATE; MALONIC ACID DERIVATIVE; PIPERIDINE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMISTRY; CONFORMATION; SYNTHESIS;

ALKYLATION; MALONATES; MOLECULAR CONFORMATION; PIPERIDINES;

EID: 0035818024     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016395o     Document Type: Article

References (31)

1. Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry, Vol. 16; Atta-ur-Rahman, Ed.; Elsevier Science Publishers B V: Amsterdam, The Netherlands, 1995; p 453. Ojima, I.; Iula, D. M. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Elsevier: Amsterdam, The Netherlands, 1999; Vol. 13. Schneider, M. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon Press Ltd: Oxford, 1996; Vol. 10, p 155.
2. Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry, Vol. 16; Atta-ur-Rahman, Ed.; Elsevier Science Publishers B V: Amsterdam, The Netherlands, 1995; p 453. Ojima, I.; Iula, D. M. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Elsevier: Amsterdam, The Netherlands, 1999; Vol. 13. Schneider, M. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon Press Ltd: Oxford, 1996; Vol. 10, p 155.
3. Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry, Vol. 16; Atta-ur-Rahman, Ed.; Elsevier Science Publishers B V: Amsterdam, The Netherlands, 1995; p 453. Ojima, I.; Iula, D. M. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Elsevier: Amsterdam, The Netherlands, 1999; Vol. 13. Schneider, M. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon Press Ltd: Oxford, 1996; Vol. 10, p 155.
4. Bailey, P. D.; Millwood, P. A.; Smith, P. D. J. Chem. Soc., Chem. Commun. 1998, 633. Wang, C. J. J.; Wuonola, M. A. Org. Prep. Proced. Int. 1992, 24, 583.
5. Bailey, P. D.; Millwood, P. A.; Smith, P. D. J. Chem. Soc., Chem. Commun. 1998, 633. Wang, C. J. J.; Wuonola, M. A. Org. Prep. Proced. Int. 1992, 24, 583.
6. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992. Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010. Little, R. D.; Masjedizadeh, M. R.; Wallquist, O.; McLoughlin, J. I. Org. React. 1995, 47, 315.
7. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992. Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010. Little, R. D.; Masjedizadeh, M. R.; Wallquist, O.; McLoughlin, J. I. Org. React. 1995, 47, 315.
8. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992. Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010. Little, R. D.; Masjedizadeh, M. R.; Wallquist, O.; McLoughlin, J. I. Org. React. 1995, 47, 315.
9. Bhardwaj, C. L.; Ireson, J. C.; Lee, J. B.; Tyler, M. J. Tetrahedron 1977, 33, 3279. Giardini, A.; Lesma, G.; Passarella, D.; Perez, M.; Silvani, A. Synlett 2001, 132.
10. Bhardwaj, C. L.; Ireson, J. C.; Lee, J. B.; Tyler, M. J. Tetrahedron 1977, 33, 3279. Giardini, A.; Lesma, G.; Passarella, D.; Perez, M.; Silvani, A. Synlett 2001, 132.
11. Two recent examples: Ariza, X.; Costa, A. M.; Faja, M.; Pineda, O.; Vilarrasa, J. Org. Lett. 2000, 2, 2809. Aiguade, J.; Hao, J.; Forsyth, C. J. Org. Lett. 2001, 3, 979.
12. Two recent examples: Ariza, X.; Costa, A. M.; Faja, M.; Pineda, O.; Vilarrasa, J. Org. Lett. 2000, 2, 2809. Aiguade, J.; Hao, J.; Forsyth, C. J. Org. Lett. 2001, 3, 979.
13. Grossman, R. B. Synlett 2001, 13.
14. β-Aminomalonates and β-amino-α-cyanocarboxylates are final intermediates in Knoevenagel condensations, wherein they undergo β-elimination of amine under very mild conditions.
15. Brown, T.; Shaw, G.; Durant, G. J. J. Chem. Soc., Perkin Trans. 1 1980, 2310.
16. Shiozaki, M.; Ishida, N.; Maruyama, H.; Hiraoka, T. Tetrahedron 1983, 39, 2399. Heitsch, H.; Wagner, A.; Yadav-Bhatnagar, N.; Griffoul-Marteau, C. Synthesis 1996, 1325.
17. Shiozaki, M.; Ishida, N.; Maruyama, H.; Hiraoka, T. Tetrahedron 1983, 39, 2399. Heitsch, H.; Wagner, A.; Yadav-Bhatnagar, N.; Griffoul-Marteau, C. Synthesis 1996, 1325.
18. Diethyl prenylmalonate: Staudinger, H.; Kreis, W.; Schilt, W. Helv. Chim. Acta 1922, 5, 743. Ethyl cinnamylcyanoacetate: Gagnon, P. E.; Boivin, J. L.; Boivin, P. A.; Jones, R. N. Can. J. Chem. 1951, 29, 182. Prenylmalononitrile: Kolsaker, P.; Storesund, H. J.; Gulbrandsen, T.; Woien, G. Acta Chem. Scand. Ser. 1983, B37, 187. A procedure developed for propargylmalononitrile was used to prepare prenylmalononitrile: Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157.
19. Diethyl prenylmalonate: Staudinger, H.; Kreis, W.; Schilt, W. Helv. Chim. Acta 1922, 5, 743. Ethyl cinnamylcyanoacetate: Gagnon, P. E.; Boivin, J. L.; Boivin, P. A.; Jones, R. N. Can. J. Chem. 1951, 29, 182. Prenylmalononitrile: Kolsaker, P.; Storesund, H. J.; Gulbrandsen, T.; Woien, G. Acta Chem. Scand. Ser. 1983, B37, 187. A procedure developed for propargylmalononitrile was used to prepare prenylmalononitrile: Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157.
20. Diethyl prenylmalonate: Staudinger, H.; Kreis, W.; Schilt, W. Helv. Chim. Acta 1922, 5, 743. Ethyl cinnamylcyanoacetate: Gagnon, P. E.; Boivin, J. L.; Boivin, P. A.; Jones, R. N. Can. J. Chem. 1951, 29, 182. Prenylmalononitrile: Kolsaker, P.; Storesund, H. J.; Gulbrandsen, T.; Woien, G. Acta Chem. Scand. Ser. 1983, B37, 187. A procedure developed for propargylmalononitrile was used to prepare prenylmalononitrile: Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157.
21. Diethyl prenylmalonate: Staudinger, H.; Kreis, W.; Schilt, W. Helv. Chim. Acta 1922, 5, 743. Ethyl cinnamylcyanoacetate: Gagnon, P. E.; Boivin, J. L.; Boivin, P. A.; Jones, R. N. Can. J. Chem. 1951, 29, 182. Prenylmalononitrile: Kolsaker, P.; Storesund, H. J.; Gulbrandsen, T.; Woien, G. Acta Chem. Scand. Ser. 1983, B37, 187. A procedure developed for propargylmalononitrile was used to prepare prenylmalononitrile: Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157.
22. Oehrlein, R.; Jaeger, V. Tetrahedron Lett. 1988, 29, 6083.
23. Abdel-Magid, A. F.; Harris, B. D.; Maryanoff, C. A. Synlett 1994, 81.
24. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
25. 2Et, Me) are assumed to have the same energetic price as interactions between H and those groups.
26. The mono-Michael adduct derived from 2c is obtained as a 3:1 E/Z mixture. Other mono-Michael adducts have also been obtained as E/Z mixtures: Grossman, R. B. Pendharkar, D. S.; Patrick, B. O. J. Org. Chem. 1999, 64, 7178.
27. The latter interactions may be worse in the TSs than in the products, as rotation to reduce the interactions is much more circumscribed in the TSs.
28. Grossman, R. B.; Rasne, R. M.; Patrick, B. O. J. Org. Chem. 1999, 64, 7173.
29. Grossman, R. B.; Pendharkar, D. S.; Rasne, R. M.; Varner, M. A. J. Org. Chem. 2000, 65, 3255.
30. Barluenga, J.; Aznar, F.; Ribas, C.; Valdés, C. J. Org. Chem. 1998, 63, 10052.
31. Grossman, R. B.; Varner, M. A.; Skaggs, A. J. J. Org. Chem. 1999, 64, 340.