Unusual gold(I)-catalyzed isomerization of 3-hydroxylated 1,5-enynes: Highly substrate-dependent reaction manifolds

Organic Letters

Volumn 7, Issue 19, 2005, Pages 4129-4132

  Gagosz, Fabien ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 25444517094     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051397k     Document Type: Article

References (20)

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15. For related studies, see: (a) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655.
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17. A fast coloration of the solution and the formation of very apolar products were observed. Under the same reaction conditions, product 3a led to the formation of the same byproducts.
18. For a review on π-nucleophilicity in C-C bond formation, see: Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77.
19. The reason for such a selectivity is still unclear, and studies to rationalize this result are underway.
20. For an example of the silver(I)-catalyzed acetylenic oxy-Cope process, see: Bluthe, N.; Gore, J.; Malacria, M. Tetrahedron 1986, 42, 1333-1344.