Cyclohydrocarbonylation-based strategy toward poly-substituted piperidines

Organic Letters

Volumn 13, Issue 9, 2011, Pages 2294-2297

  Arena, Giada ^a   Zill, Nicolas ^b   Salvadori, Jessica ^a   Girard, Nicolas ^b   Mann, André ^b   Taddei, Maurizio ^a  

^a UNIVERSITY OF SIENA   (Italy)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBON; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

HYDROCARBONS, CYCLIC; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PIPERIDINES;

EID: 79955578898     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200557r     Document Type: Article

References (30)

1. Reviews: Ojima, I. Pure App. Chem. 2002, 74, 159-166
2. Chiou, W-H; Lee, S.-Y.; Ojima, I. Can. J. Chem. 2005, 83, 681-692
3. Varchi, G.; Ojima, I. Curr. Org. Chem. 2006, 10, 1341-1362 Recent papers: Chiou, W-H; Mizutani, N.; Ojima, I. J. Org. Chem. 2007, 72, 1871-1882
4. Chiou, W.-H.; Lin, G.-H.; Hsu, C.-C; Chaterpaul, S. J.; Ojima, I. Org. Lett. 2009, 11, 2659-2662
5. Chiou, W.-H.; Lin, G-H; Liang, C.-W. J. Org. Chem. 2010, 75, 1748-1751
6. Airiau, E.; Spangenberger, T.; Girard, N; Schoenfelder, A.; Salvadori, J.; Taddei, M.; Mann, A. Chem.-Eur. J. 2008, 14, 10938-10948
7. Airiau, E.; Girard, A.; Mann, A.; Salvadori, J.; Taddei, M. Org. Lett. 2009, 11, 5314-5317
8. Salvadori, J.; Airiau, E.; Girard, N.; Mann, A.; Taddei, M. Tetrahedron. 2010, 66, 3749-3753
9. Agami, C.; Couty, F; Evano, G Tetrahedron: Asymmetry 2000, 11, 4639-4643
10. Recent reviews on piperidine synthesis: Cossy, J. Chem. Rec. 2005, 5, 70-80
11. Escolano, C.; Amat, M.; Bosch, J. Chem.-Eur. J. 2006, 12, 8198-8207
12. Kaellstroem, S.; Leino, R. Bioorg. Med. Chem. 2008, 16, 601-635
13. De Risi, C.; Fanton, G.; Pollini, G. P.; Trapella, C.; Valente, F.; Zanirato, V. Tetrahedron: Asymmetry 2008, 19, 131-155
14. Valaivan, T.; Winotapan, C.; Bancphavichit, V.; Shinada, T.; Ohfune, Y. J. Org. Chem. 2005, 70, 3464-3471
15. Reviews: Kargbo, R. B; Cook, G. R. Curr. Org. Chem. 2007, 11, 1287-1309
16. Kouznetsov, V. V.; Mendez, L. Y. V. Synthesis 2008, 491-506
17. Roy, U. K.; Roy, S. Chem. Rev. 2010, 110, 2472-2535 Selected recent papers: Jang, T. S.; Ku, I. W.; Jang, M. S.; Keum, G.; Kang, S. B.; Chung, B. Y.; Kim, Y. Org. Lett. 2006, 8, 195-198
18. Black, D. A; Arndtsen, B. A. Org. Lett. 2006, 8, 1991-1993
19. Babu, S. A.; Yasuda, M.; Baba, A. Org. Lett. 2007, 9, 405-408
20. Kim, S. H.; Lee, H. S.; Kim, K. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 1696-1698
21. Kim, S. H.; Kim, S. H.; Lee, K. Y; Kim, J. N. Tetrahedron Lett. 2009, 50, 5744-5747
22. Delaye, P. O.; Pradhan, T. K.; Lambert, E.; Vasse, J.-L.; Szymoniak, J. Eur. J. Org. Chem. 2010, 3395-3406
23. Thirupathi, P.; Kim, S. S. Tetrahedron. 2010, 66, 8623-8628
24. Valaivan, T.; Winotapan, C.; Shinada, T.; Ohfune, Y. Tetrahedron Lett. 2001, 42, 9073-9076
25. Allylation chemistry was carried out at rt (20 °C), as lower temperatures decreased yields without improvements in stereoselectivity.
26. The observation that either diastereomer led to the same stereoisomer suggests the formation of an intermediate hydroxy iminium ion. See: Poupon, E.; Franĉois, D.; Kunesch, N.; Husson, H.-P. J. Org. Chem. 2004, 69, 3836-3841
27. Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703
28. 4 was reported to remove (-)-4-isopropyl-2-aminoindanol from 2,4,6-trisubstituted piperidines prepared using this chiral auxiliary: Kobayashi, T.; Hasegawa, F.; Tanaka, K.; Katsumura, S. Org. Lett. 2006, 8, 3813-3816
29. This is the first total synthesis of this alkaloid. An attempted structure determination has been previously described: Daly, J. W.; Myers, C. W.; Whittaker, N. Toxicon 1987, 25, 1023-1030
30. Stoye, A.; Quandt, G.; Brunnhöfer, B.; Kapatsina, E.; Baron, J.; Fisher, A.; Weymann, M.; Kunz, H. Angew. Chem., Int. Ed. 2009, 48, 2208-2230