A concise enantioselective synthesis of (+)-endo-brevicomin accomplished by a tellurium/metal exchange reaction

Journal of the Brazilian Chemical Society

Volumn 19, Issue 5, 2008, Pages 811-812

  Ferrarini, Renan S ^a   Princival, Jefferson L ^a   Comasseto, João V ^a   Dos Santos, Alcindo A ^b  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF SÃO CARLOS   (Brazil)

Author keywords

Epoxide opening; Homoenolate; Tellurium lithium exchange

Indexed keywords

EID: 46749107157     PISSN: 01035053     EISSN: 16784790     Source Type: Journal    
DOI: 10.1590/S0103-50532008000500002     Document Type: Article

References (20)

1. Abou, A.; Foubelo, F.; Yus, M.; Tetrahedron 2007, 63, 6625.
2. Chen, W.; Zhao, X.; Lu, L.; Cohen, T.; Org. Lett. 2006, 8, 2087;
3. Deng, K.; Bensari, A.; Cohen, T.; J. Am. Chem. Soc. 2002, 124, 12106;
4. Deng, K.; Bensari-Bouguerra, A.; Whetstone, J.; Cohen, T.; J. Org. Chem. 2006, 71, 2360;
5. Cheng, D.; Shu, S.; Yu, Z.; Cohen, T.; J. Am. Chem. Soc. 2001, 123, 30.
6. Comasseto, J. V.; Barrientos-Astigarraga, R. E.; Aldrichimica Acta 2000, 33, 66;
7. Petragnani, N.; Stefani, H. A.; Tellurium in Organic Synthesis, Second, Updated and Enlarged Edition; Elsevier: Amsterdam, 2007;
8. Petragnani, N.; Stefani, H. A.; Tetrahedron 2005, 61, 1613;
9. Zeni, G.; Lüdtke, D. S.; Panatieri, S. B.; Braga, A. L.; Chem. Rev. 2006, 106, 1032.
10. Princival, J. L.; Barros, S. M. G.; Comasseto, J. V.; Dos Santos, A. A.; Tetrahedron Lett. 2005, 46, 4423;
11. Bassora, B. K.; Da Costa, C. E.; Gariani, R. A.; Comasseto, J. V.; Dos Santos, A. A.; Tetrahedron Lett. 2007, 48, 1485.
12. Dos Santos, A. A.; Ferrarini, R. S.; Princival, J. L.; Comasseto, J. V.; Tetrahedron Lett. 2006, 47, 8933.
13. Dos Santos, A. A.; Comasseto, J. V.; J. Braz. Chem. Soc. 2005, 16, 511.
14. Dos Santos, A. A.; Princival, J. L.; Comasseto, J. V.; Barros, S. M. G.; Brainer Neto, J. E.; Tetrahedron 2007, 63, 5167.
15. Mori, K.; Seu, Y.-B.; Tetrahedron 1985, 41, 3429;
16. Yus, M.; Ramón, D. J.; J. Org. Chem. 1992, 57, 750;
17. Burke, S. D.; Müller, N.; Beaudry, C. M.; Org. Lett. 1999, 1, 1827;
18. Kim, M.-J.; Choi, Gil-B.; Kim, J.-Y.; Kim, H.-J.; Tetrahedron Lett. 1995, 36, 6253;
19. Taylor, R. J. K.; Organocopper Reagents A Practical Approach; Oxford University Press: New York, 1994, and references mentioned therein.
20. Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharples, K. B.; J. Am. Chem. Soc. 1981, 103, 6237.