2-Trimethylsilylethanesulfonyl (SES) versus tosyl (Ts) protecting group in the preparation of nitrogen-containing five-membered rings. A novel route for the synthesis of substituted pyrrolines and pyrrolidines

Journal of Organic Chemistry

Volumn 72, Issue 4, 2007, Pages 1518-1521

  Declerck, Valérie ^a,c   Allouchi, Hassan ^b   Martinez, Jean ^a   Lamaty, Frédéric ^a  

^a CNRS   (France)

^b EA 3857   (France)

^c WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; HYDROGENATION; NITROGEN; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

AMINE PYRROLIDINES; DIASTEREOSELECTIVITY; PYRROLES; PYRROLIDINES;

ORGANIC COMPOUNDS;

NITROGEN; PYRROLIDINE DERIVATIVE; PYRROLINE DERIVATIVE; SULFONE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ALKYLATION; ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEPROTECTION REACTION; ORGANIC CHEMISTRY;

EID: 33846998670     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062239p     Document Type: Article

References (30)

1. Bertenshaw, S.; Kahn, M. Tetrahedron Lett. 1989, 30, 2731-2732.
2. Richter, H.; Jung, G. Tetrahedron Lett. 1998, 39, 2729-2730.
3. Balan, D.; Adolfsson, H. J. Org. Chem. 2001, 66, 6498-6501.
4. Balan, D.; Adolfsson, H. J. Org. Chem. 2002, 67, 2329-2334.
5. Balan, D.; Adolfsson, H. Tetrahedron Lett. 2003, 44, 2521-2524.
6. Ribière, P.; Enjalbal, C.; Aubagnac, J.-L.; Yadav-Bhatnagar, N.; Martinez, J.; Lamaty, F. J. Comb. Chem. 2004, 6, 464-467.
7. Ribière, P.; Yadav-Bhatnagar, N.; Martinez, J.; Lamaty, F. QSAR Comb. Sci. 2004, 23, 911-914.
8. Declerck, V.; Ribière, P.; Martinez, J.; Lamaty, F. J. Org. Chem. 2004, 69, 8372-8381.
9. Vasudevan, A.; Tseng, P.-S.; Djuric, S. W. Tetrahedron Lett. 2006, 47, 8591-8593.
10. For examples in the case of five-membered rings, see: (a) Chang, M.-Y.; Pai, C.-L.; Kung, Y.-H. Tetrahedron Lett. 2006, 47, 855-859.
11. (b) Dondas, H. A.; Clique, B.; Cetinkaya, B.; Grigg, R.; Kilner, C.; Morris, J.; Sridharan, V. Tetrahedron 2005, 61, 10652-10666.
12. (c) Grigg, R.; Martin, W.; Morris, J.; Sridharan, V. Tetrahedron 2005, 61, 11380-11392.
13. (d) Kim, B. G.; Snapper, M. L. J. Am. Chem. Soc. 2006, 128, 52-53.
14. (e) Morita, N.; Krause, N. Org. Lett. 2004, 6, 4121-4123.
15. (f) Ma, S.; Yu, F.; Gao, W. J. Org. Chem. 2003, 68, 5943-5949.
16. (a) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041.
17. (b) Nandi, B.; Kundu, N. G. Org. Lett. 2000, 2, 235-238.
18. (c) Kundu, N. G.; Nandi, B. J. Org. Chem. 2001, 66, 4563-4575.
19. Weinreb, S. M.; Demko, D. M.; Lessen, T. A.; Demers, J. P. Tetrahedron Lett. 1986, 27, 2099-2102.
20. Ribière, P.; Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev. 2006, 106, 2249-2269.
21. Balan, D.; Adolfsson, H. Tetrahedron Lett. 2004, 45, 3089-3092.
22. Kozlowski, M. C.; Bartlett, P. A. J. Org. Chem. 1996, 61, 7681-7696.
23. Parker, K. A.; Mindt, T. L. Org. Lett. 2002, 4, 4265-4268.
24. Boger, D. L.; Ledeboer, M. W.; Kume, M. J. Am. Chem. Soc. 1999, 121, 1098-1099.
25. Laughlin, R. G. J. Am. Chem. Soc. 1967, 89, 4268-4271.
26. Lee, K. Y.; Na, J. E.; Lee, J. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2004, 25, 1280-1282.
27. For a review on the RCM approach for the preparation of aromatic compounds, see: Donohoe, T. J.; Orr, A. J.; Bingham, M. Angew. Chem., Int. Ed. 2006, 45, 2664-2670.
28. For examples of pyrrole synthesis via the RCM route, see: (a) Yang, C.; Murray, W. V.; Wilson, L. J. Tetrahedron Lett. 2003, 44, 1783-1786.
29. (b) Dieltiens, N.; Stevens, C. V.; De Vos, D.; Allaert, B.; Drozdzak, R.; Verpoort, F. Tetrahedron Lett. 2004, 45, 8995-8998.
30. (c) Dieltiens, N.; Stevens, C. V.; Allaert, B.; Verpoort, F. ARKIVOC 2005, 92-97.