Synthesis and reactivity of a 3-vinylidenepiperidine as a model study of α-allenic amines

Heterocycles

Volumn 43, Issue 11, 1996, Pages 2415-2424

  Solé, Daniel ^a   García Rubio, Silvina ^a   Bosch, Joan ^a   Bonjoch, Josep ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0842287911     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-96-7563     Document Type: Article

References (35)

1. D. Solé, J. Bonjoch, S. García-Rubio, R. Suriol, and J. Bosch, Tetrahedron Lett., 1996, 37, 5213.
2. J. Bosch, J. Bonjoch, and M. Amat, 'The Alkaloids: Strychnos Alkaloids,' Vol. 48, ed. by G. A. Cordell, Academic Press, New York, 1996, pp. 75-189.
3. K. Bojthe-Horvath, A. Kocsis, I. Mathe, J. Tamas, and O. Clauder, Acta Pharm. Hung., 1974, 44, Suppl., 66 (Chem. Abstr., 1974, 81, 136347y)
4. K. Bojthe-Horvath, A. Kocsis, I. Mathe, J. Tamas, and O. Clauder, Acta Pharm. Hung., 1974, 44, Suppl., 66 (Chem. Abstr., 1974, 81, 136347y)
5. C. Djerassi, Y. Nakagawa, J. M. Wilson, H. Budzikiewicz, B. Gilbert, and L. D. Antonaccio, Experientia, 1963, 19, 467.
6. G. Massiot, P. Thépenier, M.-J. Jacquier, J. Lounkokobi, C. Mirand, M. Zèches, L. L. Men-Olivier, and C. Delaude, Tetrahedron, 1983, 39, 3645.
7. For the intramolecular addition of propargylic silanes to enones in the carbocyclic series, see D. Schinzer, Synthesis, 1988, 263. For more recent applications, see: D. Schinzer and K. Ringe, Synlett, 1994, 463; D. Schinzer, K. Ringe, P. G. Jones, and D. Döring, Tetrahedron Lett., 1995, 36, 4051.
8. For the intramolecular addition of propargylic silanes to enones in the carbocyclic series, see D. Schinzer, Synthesis, 1988, 263. For more recent applications, see: D. Schinzer and K. Ringe, Synlett, 1994, 463; D. Schinzer, K. Ringe, P. G. Jones, and D. Döring, Tetrahedron Lett., 1995, 36, 4051.
9. For the intramolecular addition of propargylic silanes to enones in the carbocyclic series, see D. Schinzer, Synthesis, 1988, 263. For more recent applications, see: D. Schinzer and K. Ringe, Synlett, 1994, 463; D. Schinzer, K. Ringe, P. G. Jones, and D. Döring, Tetrahedron Lett., 1995, 36, 4051.
10. G. Stork and S. M. McElvain, J. Am. Chem. Soc., 1947, 69, 971.
11. This procedure improves the previously reported preparation of 3 by DIBAH reduction of the methyl ester analogue of 1 : A. Barco, S. Benetti, C. De Risi, G. P. Pollini, R. Romagnoli, G. Spalluto, and V. Zanirato, Tetrahedron, 1994, 50, 2583. See also: A. Barco, S. Benetti, A. Casolari, G. P. Pollini, and G. Spalluto, Tetrahedron Lett., 1990, 31, 3039.
12. This procedure improves the previously reported preparation of 3 by DIBAH reduction of the methyl ester analogue of 1 : A. Barco, S. Benetti, C. De Risi, G. P. Pollini, R. Romagnoli, G. Spalluto, and V. Zanirato, Tetrahedron, 1994, 50, 2583. See also: A. Barco, S. Benetti, A. Casolari, G. P. Pollini, and G. Spalluto, Tetrahedron Lett., 1990, 31, 3039.
13. After we had concluded the experimental work, Overman reported an alternative method for the preparation of alcohol (2), its oxidation to aldehyde (3), and the conversion of the latter to the enone (4): M. Lögers, L. E. Overman, and G. S. Welmaker, J. Am. Chem. Soc., 1995, 117, 9139.
14. 12 with methyltriphenoxyphosphonium iodide in DMF.
15. W. J. Klaver, M. J. Moolenaar, H. Hiemstra, and W. N. Speckamp, Tetrahedron, 1988, 44, 3805.
16. H. Mastalerz, J. Org. Chem., 1984, 49, 4092.
17. T. N. Mitchell and U. Schneider, J. Organomet. Chem., 1991, 405, 195.
18. 13C nmr analysis of the stereochemistry of 3-alkylidenepiperidines or analogues, see: G. Van Binst and D. Tourẃ, Org. Magn. Reson., 1972, 4, 625; M. R. Uskokovic, R. L. Lewis, J. J. Partridge, C. W. Desprèaux, and D. L. Pruess, J. Am. Chem. Soc., 1979, 101, 6742; M.-L. Bennasar and J. Bosch, Tetrahedron, 1986, 42, 637.
19. 13C nmr analysis of the stereochemistry of 3-alkylidenepiperidines or analogues, see: G. Van Binst and D. Tourẃ, Org. Magn. Reson., 1972, 4, 625; M. R. Uskokovic, R. L. Lewis, J. J. Partridge, C. W. Desprèaux, and D. L. Pruess, J. Am. Chem. Soc., 1979, 101, 6742; M.-L. Bennasar and J. Bosch, Tetrahedron, 1986, 42, 637.
20. 13C nmr analysis of the stereochemistry of 3-alkylidenepiperidines or analogues, see: G. Van Binst and D. Tourẃ, Org. Magn. Reson., 1972, 4, 625; M. R. Uskokovic, R. L. Lewis, J. J. Partridge, C. W. Desprèaux, and D. L. Pruess, J. Am. Chem. Soc., 1979, 101, 6742; M.-L. Bennasar and J. Bosch, Tetrahedron, 1986, 42, 637.
21. 1H nmr analysis of the stereochemistry of 3-alkylidenepiperidines or analogues, see: W. R. Ashcroft and J. A. Joule, Tetrahedron Lett., 1980, 21, 2341; J. C. Nouls, G. Van Binst, and R. H. Martin, Tetrahedron Lett., 1967, 4065.
22. 1H nmr analysis of the stereochemistry of 3-alkylidenepiperidines or analogues, see: W. R. Ashcroft and J. A. Joule, Tetrahedron Lett., 1980, 21, 2341; J. C. Nouls, G. Van Binst, and R. H. Martin, Tetrahedron Lett., 1967, 4065.
23. For a similar conformational effect, see: I. Ninomiya, T. Naito, O. Miyata, T. Shinada, E. Winterfeldt, R. Freund, and T. Ishida, Heterocycles, 1990, 30, 1031.
24. J. A. Verdone, J. A. Mangravite, N. M. Scarpa, and H. G. Kuivila, J. Am. Chem. Soc., 1975, 97, 843
25. The downfield shift of this proton in piperidines with an axial 3-vinyl substituent has previously been observed in the meroquinene series: S. Hanessian, A.-M. Faucher, and S. Léger, Tetrahedron, 1990, 46, 231; B. Danieli, G. Lesma, M. Mauro, G. Palmisano, and D. Passarella, Tetrahedron: Asymmetry, 1990, 1, 793
26. The downfield shift of this proton in piperidines with an axial 3-vinyl substituent has previously been observed in the meroquinene series: S. Hanessian, A.-M. Faucher, and S. Léger, Tetrahedron, 1990, 46, 231; B. Danieli, G. Lesma, M. Mauro, G. Palmisano, and D. Passarella, Tetrahedron: Asymmetry, 1990, 1, 793
27. S. Hanessian and R. Léger, Synlett, 1992, 402.
28. M. Yamamoto, S. Irie, M. Miyashita, S. Kohmoto, and K. Yamada, Chem. Lett., 1989, 221; S. Kim and P. L. Fuchs, J. Am. Chem. Soc., 1993, 115, 5934.
29. M. Yamamoto, S. Irie, M. Miyashita, S. Kohmoto, and K. Yamada, Chem. Lett., 1989, 221; S. Kim and P. L. Fuchs, J. Am. Chem. Soc., 1993, 115, 5934.
30. Y. Ueno, H. Sano, and M. Okawara, Synthesis, 1980, 1011.
31. M. Ferrer, F. Sánchez-Baeza, A. Messeguer, A. Diez, and M. Rubiralta, J. Chem. Soc., Chem. Commun., 1995, 293.
32. Initial attempts to obtain allylic alcohol (12) by hydroboration of allene (8) with 9-BBN were abandoned because of the reduction of the carbonyl group.
33. J. H. Babler and D. O. Olsen, Tetrahedron Lett., 1974, 351.
34. For the isomerization of Z/E isomers in the Strychnos field, see: M. E. Kuehne and F. Xu, J. Org. Chem., 1993, 58, 7490.
35. This acetate (13) was the sole compound isolated together with the starting alcohol, when the acetylation was carried out under basic conditions (AcCl, pyridine).