A Reductive Cyclization of 1,6- and 1,7-Enynes

Journal of the American Chemical Society

Volumn 109, Issue 10, 1987, Pages 3161-3163

  Trost, Barry M ^a   Rise, Frode ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001342781     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00244a059     Document Type: Article

References (8)

1. Intramolecular carbalkylation-carbonylation using stoichiometric cobalt complexes has become known as the Pauson-Khand reaction. See: Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans. 1 1973, 977. Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436. Billington, D. C.; Pauson, P. L. Organometallics 1982,1, 1560. Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985. 26. 4851.
2. For stoichiometric titanium-mediated reductive cyclizations, see: Nugent, W. A.; Calabrese, J. C. J. Am. Chem. Soc. 1984, 106, 6422. This method is reported to fail with terminal acetylenes.
3. For a stoichiometric zirconium-mediated reductive cyclization, see: Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A. J. Am. Chem. Soc. 1985, 107, 2568. Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27. 2829.
4. For Pd- and Rh-catalyzed cyclizations of dienes, see: Grigg, R.; Malone, J. F.; Mitchell, T. R. B.; Ramasubbu, A.; Scott, R. M. J. Chem. Soc., Perkin Trans. 1 1984, 1745. In the Pd reactions, use of HC1 in refluxing chloroform is required. The same group has reported cyclizations of vinyl bromides onto olefins by using Pd catalysts. See: Grigg, R.; Stevenson, P.; Worakun, T. Chem. Commun. 1984, 1073.
5. (a) Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1985, 197, 1781; Tetrahedron Lett. 1985, 26, 4887. Trost, B. M.; Chen, S. F. J. Am. Chem. Soc. 1986, 108, 6053. Trost, B. M.; Chung, J. Y. L. J. Am. Chem. Soc. 1985, 107, 4586.
6. For a reduction using PMHS in a Pd(0) reaction, see: Keinan, E.; Greenspoon, N. J. Org. Chem. 1983, 48, 3545.
7. Cf. Heck reaction, see: Heck, R. F. Org. React. 1982, 27, 345.
8. Maitlis, P. M.; Espinet, P.; Russell, M. J. H.; Compr, Organomet. Chem. 1982, 6, 250–252, 340–342.