Silver-catalyzed cyclization of acetylenic alcohols and acids: A remarkable accelerating effect of a propargylic C-O bond

New Journal of Chemistry

Volumn 23, Issue 8, 1999, Pages 803-805

  Dalla, V ^a   Pale, P ^b  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; HETEROCYCLIC COMPOUND; SILVER; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; NONHUMAN; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032793153     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903587g     Document Type: Article

References (15)

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3. For a recent review on lactones, see: G. Rousseau, Tetrahedron, 1996, 52, 2577.
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10. V. Dalla and P. Pale, Tetrahedron Lett., 1994, 35, 3525; J. Nokami, H. Ohtsuki, Y. Sakamoto, M. Mitsuoka and N. Kunieda, Chem. Lett., 1992, 1647.
11. P. Pale, J. Chuche, J. Bouquant, P. Vogel and P. A. Carrupt, Tetrahedron, 1994, 50, 8035; V. Dalla and P. Pale, Tetrahedron Lett., 1996, 37, 2777; V. Dalla and P. Pale, Tetrahedron Lett., 1996, 37, 2781; V. Dalla and P. Pale, Tetrahedron Lett., 1992, 33, 7857.
12. P. Pale, J. Chuche, J. Bouquant, P. Vogel and P. A. Carrupt, Tetrahedron, 1994, 50, 8035; V. Dalla and P. Pale, Tetrahedron Lett., 1996, 37, 2777; V. Dalla and P. Pale, Tetrahedron Lett., 1996, 37, 2781; V. Dalla and P. Pale, Tetrahedron Lett., 1992, 33, 7857.
13. P. Pale, J. Chuche, J. Bouquant, P. Vogel and P. A. Carrupt, Tetrahedron, 1994, 50, 8035; V. Dalla and P. Pale, Tetrahedron Lett., 1996, 37, 2777; V. Dalla and P. Pale, Tetrahedron Lett., 1996, 37, 2781; V. Dalla and P. Pale, Tetrahedron Lett., 1992, 33, 7857.
14. P. Pale, J. Chuche, J. Bouquant, P. Vogel and P. A. Carrupt, Tetrahedron, 1994, 50, 8035; V. Dalla and P. Pale, Tetrahedron Lett., 1996, 37, 2777; V. Dalla and P. Pale, Tetrahedron Lett., 1996, 37, 2781; V. Dalla and P. Pale, Tetrahedron Lett., 1992, 33, 7857.
15. In such transition metal-assisted electrophilic cyclizations, the accepted mechanism postulates a previous activation of the π system by coordination to the metal cation, rendering the so-formed complex electrophilic enough for further reaction with a nucleophile. See, for example: K. Utimoto, Y. Fukuda and H. Nozaki, Heterocycles, 1987, 25, 297.