A novel C2-symmetric 2,6-Diallylpiperidine carboxylic acid methyl ester as a promising chiral building block for piperidine-related alkaloids

Organic Letters

Volumn 4, Issue 20, 2002, Pages 3459-3462

  Takahata, Hiroki ^a   Ouchi, Hidekazu ^a   Ichinose, Motohiro ^b   Nemoto, Hideo ^b  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,6 DIALLYLPIPERIDINE CARBOXYLIC ACID METHYL ESTER; 2,6-DIALLYLPIPERIDINE CARBOXYLIC ACID METHYL ESTER; ALKALOID; ESTER; GLUTARALDEHYDE; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKALOIDS; ESTERS; GLUTARAL; MOLECULAR STRUCTURE; PIPERIDINES;

EID: 0037015420     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0265620     Document Type: Article

References (19)

1. Rubiralta, M.; Giralt, E.; Diez, A. Piperidine. Structure, Preparation, Reactivity and Synthetic Applications of Piperidine and Its Derivatives; Elsevier: Amsterdam, 1991.
2. For a recent review, see: Laschat, S.; Dickner, T. Synthesis 2000, 1781.
3. Takahata, H.; Takahashi, S.; Kouno, S.; Momose, T. J. Org. Chem. 1998, 63, 2224.
4. Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1997, 38, 2417.
5. (a) Takahata, H.; Yotsui, Y.; Momose, T. Tetrahedron 1998, 54, 13505.
6. (b) Takahata, H.; Shimizu, M. Amino Acids, in press.
7. Attempts with other alkyl chloroformates such as ethyl, benzyl, and trichloromethyl chlorotornates were unsuccessful.
8. (a) Tawara, J. N.; Blokhin, A.; Foderaro, T. A.; Stermitz, F. R.; Hope, H. J. Org. Chem. 1993, 58, 4813.
9. (b) Adamo, M. F. A.; Aggarwal, V. K.; Sage, M. A. Synth. Commun. 1999, 29, 1747.
10. Recent synthesis: (a) Reding, M. T.; Buchwald, S. L. J. Org. Chem. 1998, 63, 6344.
11. (b) Wilkinson, T. J.; Stehle, N. W.; Beak, P. Org. Lett. 2000, 2, 155.
12. (c) Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 2911.
13. Takahata, H.; Kubota, M.; Takahashi, S.; Momose, T. Tetrahedron: Asymmetry 1996, 7, 3047.
14. (a) Yue, C.; Nicolay, F.; Royer, J.; Husson, H. P. Tetrahedron 1994, 50, 3139.
15. (b) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032.
16. Isolation and identification; Denne, W. A.; Johns, S. R.; Lamberton, J. A.; Mathieson, A. McL.; Suares, H. Tetrahedron Lett. 1972, 18, 1767.
17. (a) David, M.; Dhimane, H.; Vanucci-Bacque, C.; Lhommet, G. J. Org. Chem. 1999, 64, 8402.
18. (b) Comins, D. L.; Hong, H. J. Am. Chem. Soc. 1993, 115, 8851.
19. Corey, E. J.; Weigel, L. O.; Floyd, D.; Bock, M. G. J. Am. Chem. Soc. 1978, 100, 2916.