Asymmetric allylation/ring closing metathesis: One-pot synthesis of benzo-fused cyclic homoallylic amines. Application to the formal synthesis of Sertraline derivatives

Organic Letters

Volumn 15, Issue 14, 2013, Pages 3770-3773

  Fustero, Santos ^a,b   Lázaro, Rubén ^a   Herrera, Lidia ^a   Rodríguez, Elsa ^a   Mateu, Natalia ^a,b   Barrio, Pablo ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

^b CENTRO DE INVESTIGACIÓN PRÍNCIPE FELIPE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; SERTRALINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINES; CATALYSIS; MOLECULAR STRUCTURE; SERTRALINE; STEREOISOMERISM;

EID: 84880540261     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4017113     Document Type: Article

References (36)

1. Yus, M.; González-Gómez, J. C; Foubelo, F. Chem. Rev. 2011, 111, 7774
2. Ding, H.; Friestad, G. K. Synthesis 2005, 2815
3. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207
4. Robak, M. T.; Herbage, M. A.; Ellman, J. A. Chem. Rev. 2010, 110, 3600
5. Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073
6. Blanchard, N.; Eustache, J. Synthesis of Natural Products Containing Medium-size Carbocycles by Ring-closing Alkene Metathesis. In Metathesis in Natural Product Synthesis; Cossy, J.; Arseniyadis, S.; Meyer, C., Eds.; Wiley-VCH: Weinheim, 2010; pp 1-43.
7. Fustero, S.; Sánchez-Roselló, M.; Rodrigo, V.; del Pozo, C.; Sanz-Cervera, J. F.; Simón, A. Org. Lett. 2006, 8, 4129
8. Fustero, S.; Sanz-Cervera, J. F.; Aceña, J. L.; Sánchez-Roselló, M. Synlett 2009, 525
9. Grainger, R. S.; Welsh, E. J. Angew. Chem., Int. Ed. 2007, 46, 5377
10. Fustero, S.; Moscardó, J.; Sánchez-Roselló, M.; Rodríguez, E.; Barrio, P. Org. Lett. 2010, 12, 5494
11. Fustero, S.; Ibañez, I.; Barrio, P.; Maestro, M. A.; Catalán, S. Org. Lett. 2013, 15, 832
12. Fustero, S.; Rodríguez, E.; Herrera, L.; Asensio, A.; Maestro, M. A.; Barrio, P. Org. Lett. 2011, 13, 6564
13. Welch, W. M.; Kraska, A. R.; Sarges, R.; Koe, B. K. J. Med. Chem. 1984, 27, 1508
14. Williams, M.; Quallich, G. Chem. Ind. (London) 1990, 10, 315
15. Quallich, G. J.; Woodall, T. M. Tetrahedron 1992, 48, 10239
16. Corey, E. J.; Gant, T. G. Tetrahedron Lett. 1994, 35, 5373
17. Johnson, B. M.; Chang, P.-T. L. Anal. Profiles Drug Subst. 1996, 24, 443
18. Lee, S. H.; Kim, I., S.; Li, Q. R.; Dong, G. R.; Jeong, L. S.; Jung, Y. H. J. Org. Chem. 2011, 76, 10011
19. Ohmiya, H.; Makida, Y.; Li, D.; Tanabe, M.; Sawamura, M. J. Am. Chem. Soc. 2010, 132, 879
20. Han, Z.; Wang, Z.; Zhang, X.; Ding, K. Angew. Chem., Int. Ed. 2009, 48, 5345
21. Alexakis, A.; Hajjaji, S. E.; Polet, D.; Rathgeb, X. Org. Lett. 2007, 9, 3393
22. Dockendorff, C.; Sahli, S.; Olsen, M.; Milhau, L.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 15028
23. Nair, V.; Rajan, R.; Rath, N. P. Org. Lett. 2002, 4, 1575
24. Lautens, M.; Rovis, T. Tetrahedron 1999, 55, 8967
25. Corey, E. J.; Gant, T. G. Tetrahedron Lett. 1994, 35, 5373
26. Fustero, S.; Rodriguez, E.; Lázaro, R.; Herrera, L.; Catalán, S.; Barrio, P. Adv. Synth. Catal. 2013, 355, 1058
27. S absolute configuration was assumed for all products in agreement with Ellman's proposed transition state; see: Cogan, D. A.; Liu, G.; Ellman, J. A. Tetrahedron 1999, 55, 8883
28. van der Sluis, M.; Broxterman, Q. B. Org. Lett. 2001, 3, 3943
29. Sun, X. W.; Xu, M. H.; Lin, G. Q. Org. Lett. 2006, 8, 4979
30. Leduc, A. B.; Kerr, M. A. Angew. Chem., Int. Ed. 2008, 47, 7945
31. Grainger, R. S.; Welsh, E. J. Angew. Chem., Int. Ed. 2007, 46, 5377
32. Forrat, V. J.; Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 2009, 20, 65
33. Fustero, S.; Monteagudo, S.; Sánchez-Roselló, M.; Flores, S.; Barrio, P.; del Pozo, C. Chem.-Eur. J. 2010, 16, 9835
34. Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278
35. Chandrasekhar, S.; Reddy, M. V. Tetrahedron 2000, 56, 1111
36. Thalén, L. K.; Zhao, D.; Sortais, J.-B.; Paetzold, J.; Hoben, C.; Bäckvall, J. E. Chem.-Eur. J. 2009, 15, 3403