Copper-catalyzed cycloisomerizations of 5-en-1-yn-3-ols

Organic Letters

Volumn 8, Issue 9, 2006, Pages 1839-1841

  Fehr, Charles ^a   Farris, Iris ^a   Sommer, Horst ^a  

^a Email:   (Switzerland)

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Indexed keywords

EID: 33646454721     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0603864     Document Type: Article

References (19)

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2. Fehr, C.; Farris I. Patent submitted (Firmenich SA; prior, 19 Jul 2005.
3. 2O, 20 °C, 2 h).
4. 2O/5% aq NaOH gave rise to mixtures of 6a, 6b, and 5. Prolonged stirring led to 5. Extensive NMR experiments and IR measurement allowed us to assign structures 6a and 6b. Moreover, the fact that both of the epimeric aldol products afford the same retro-aldol product 5 proves that 6a and 6b differ only in the configuration of the OH-bearing center.
5. (a) Harrak, Y.; Blaszykowski, C.; Bernard M.; Cariou, K.; Mainetti, E.; Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
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7. Soriano, E.; Marco-Contelles, J. J. Org. Chem. 2005, 70, 9345.
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13. Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
14. For nucleophilic additions to copper-coordinated alkynes, see: Bouyssi, D.; Monteiro, N.; Balme, G. Tetrahedron Lett. 1999, 40, 1297.
15. Monteiro, N.; Balme, G.; Gore, J. Synlett 1992, 227.
16. Patil, N. T.; Wu, H.; Yamamoto, Y. J. Org. Chem. 2005, 70, 4531 and references therein.
17. For a gold-catalyzed cyclopropanation/alkyl shift of a 1-en-5-yne, see: Luzung, M. R.; Markham, J. P.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 10858.
18. See also: Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 11806.
19. In the case of 1ab, the epimerization of the propargylic center via a carbocation may be facilitated by the presence of the neighboring OH group.