Enantioselective addition of terminal alkynes to isolated isoquinoline iminiums

Organic Letters

Volumn 8, Issue 1, 2006, Pages 143-146

  Taylor, Alexander M ^a   Schreiber, Stuart L ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 30944433443     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0526165     Document Type: Article

References (17)

1. Taylor, S. J.; Taylor, A. M.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 1681.
2. (a) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535.
3. (b) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763.
4. Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784.
5. Examples of copper-catalyzed enantioselective reactions include: (a) Koradin, C.; Gommermann, N.; Polborn, K.; Knochel, P. Chem. Eur. J. 2003, 9, 2797.
6. (b) Li, C.-J.; Wei, C. J. Am. Chem. Soc. 2002, 124, 5638.
7. (c) Fu, G. C.; Suárez, A.; Downey, C. W. J. Am. Chem. Soc. 2005, 127, 11244.
8. (a) Böhme, H.; Haake, M. In Iminium Salts in Organic Chemistry; Taylor, E. C., Ed.; Advances in Organic Chemistry: Methods and Results; John Wiley & Sons: New York, 1976; Vol. 1, p 112.
9. (b) Thiessen, L. M. Tetrahedron Lett. 1974, 15, 59.
10. (c) Onaka, T. Tetrahedron Lett. 1971, 12, 4395.
11. See the Supporting Information for a general procedure.
12. (a) Blackwell, H. E.; Perez, L.; Stavenger, R. A.; Tallarico, J. A.; Eatough, E. C.; Foley, M. A.; Schreiber, S. L. Chem. Biol. 2001, 8, 1167.
13. (b) Clemons, P. A.; Koehler, A. N.; Wagner, B. K.; Sprigings, T. G.; Spring, D. R.; King, R. W.; Schreiber, S. L.; Foley, M. A. Chem. Biol. 2001, 8, 1183.
14. (c) Reference 1.
15. (a) Aladesamm, A. J., et al. J. Nat. Prod. 1983, 46, 127.
16. (b) Meyers, A. I., et al. Tetrahedron. 1987, 43, 5095.
17. Data shown in the Supporting Information. Preliminary experiments conducted with Ethan Perlstein.