Pd-Catalyzed Cycloisomerization to 1,2-Dialkylidenecycloalkanes. 2. Alternative Catalyst System

Journal of the American Chemical Society

Volumn 116, Issue 10, 1994, Pages 4268-4278

  Romero, Donna L ^a   Rise, Frode ^a   Trost, Barry M ^b  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001418081     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00089a016     Document Type: Article

References (17)

1. Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc, preceding paper in this issue and references therein.
2. Tsuji, J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ley, S. V., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 7, Chapter 3.4, pp 444-468.
3. Werner, H.; Bertleff, W. Chem. Ber. 1983, 116, 823. Also see: Zudin, V. N.; Chinakov, V. D.; Nekipelov, V. M.; Likholobov, V. A.; Yermakov, Y. I. J. Organomet. Chem. 1985, 289, 425.
4. For some examples of the synthesis of dialkylidenecyclopentanes and their use in Diels-Alder reactions, see: Sustmann, R.; Daute, P.; Sauer, R.; Sommer, A.; Trahanovsky, W. S. Chem. Ber. 1989, 122, 1551. Barco, A.; Benetti, S.; Casolari, A.; Manfredini, S.; Pollini, G. P.; Polo, E.; Zanirato, V. Tetrahedron 1989, 45, 3935. Baran, J.; Mayr, H. Tetrahedron 1989, 45, 3347. Baran, J.; Klein, H.; Schade, C.; Will, E.; Koschinsky, R.; Bàuml, E.; Mayr, H. Tetrahedron 1988, 44, 2181. Fagan, P. J.; Nugent, W. A. J. Am. Chem. Soc. 1988,110, 2310. Nugent, W. A.; Thorn, D. L.; Harlow, R. L. J. Am. Chem. Soc. 1987, 109, 2788. Negishi, E.; Cederbaum, F. E.; Takashi, T. Tetrahedron Lett. 1986, 27, 2829. Kozikowski, A. P.; Jung, S. H. Tetrahedron Lett. 1986, 27, 3227. Nugent, W. A.; Calabrese, J. C. J. Am. Chem. Soc. 1984,106,6422. Block, E.; Aslam, M. J. J. Am. Chem. Soc. 1983, 105, 6165.
5. For preliminary reports of portions of this work, see: Trost, B. M.; Lee, D. C.; Rise, F. Tetrahedron Lett. 1989, 30, 651. Trost, B. M.; Lee, D. C. J. Org. Chem. 1989, 54, 2271.
6. Trost, A. M.; Molander, G. A. J. Am. Chem. Soc. 1981, 103, 5969.
7. Trost, A. M.; Edstrom, E. D.; Carter-Petillo, M. B. J. Org. Chem. 1989, 54, 4489.
8. Gree, R.; Kessabi, J.; Mossel, P.; Martelli, J.; Carrie, R. Tetrahedron Lett. 1984, 25, 3697. Franck, R. W.; Argade, S.; Subramanian, C. S.; Frechet, D. M. Tetrahedron Lett. 1985,3187. Schlessinger, R. H.; Wong, J. W.; Poss, M. A.; Springer, J. P. J. Org. Chem. 1985, 50, 3951. Sternbach, D.; Rossana, D. M.; Onan, K. D. Tetrahedron Lett. 1985,26,591. Jones, R. C. F.; Tunnicliffe, J. H. Tetrahedron 1985, 50, 3421. Marshall, J. A.; Andra, J. E.; Grote, J. J. Org. Chem. 1986, 51, 1155. McDougal, P. G.; Rico, J. G.; Van Derveer, D. J. Org. Chem. 1986, 51,4491. For more recent references, see: Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988,110, 3257. Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988,110, 4625. Herezegh, P.; Zsely, M.; Szilagyi, L.; Bognar, R. Tetrahedron Lett. 1988, 29, 481. Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1988, 110, 4074. Reitz, A. B.; Jordan, A. D., Jr.; Maryanoff, B. E. J. Org. Chem. 1987, 52, 4800. Marshall, J. A.; Shearer, B. G.; Crooks, S. L. J. Org. Chem. 1987, 52, 1236.
9. For effects on intramolecular reactions, see: Roush, W. R. J. Am. Chem. Soc. 1980, 102, 1390. Roush, W. R.; Hall, S. E. J. Am. Chem. Soc. 1981, 103, 5200. Funk, R. L.; Zeller, W. E. J. Org. Chem. 1982, 47, 180. Huaina, M.; Uei, M. J. Am. Chem. Soc. 1982,104,4251. Roush, W. R.; Hall, S. E. J. Org. Chem. Soc. 1982, 47,4611. Boeckman, R. K.; Barta, T. E. Org. Chem. 1985, 50, 3421. Roush, W. R.; Kageyama, M.; Riva, R.; Brown, B. B.; Warmus, J. S.; Moriarty, K. J. J. Org. Chem. 1991, 56, 1192.
10. Sustmann, R.; Sauer, J. Angew. Chem., Int. Ed. Engl. 1980, 19, 779. Taber, D. F. Intramolecular Diets-Alder Reactions and Alder ene Reactions; Springer-Verlag: New York, 1984. Ciganek, E. Org. React. 1984, 32, 1. Fallis, A. G. Can. J. Chem. 1984, 62,183. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., Vol. 5, Chapter 4.4, pp 513-550.
11. Also see: Ichihara, A.; Kimura, R.; Yamada, S.; Sakamura, S. J. Am. Chem. Soc. 1980, 102, 6353 and ref 4.
12. Denmark, S. E.; Jones, T. K. J. Org. Chem. 1982, 47, 4595.
13. Trost, B. M.; Vercauteren, J. Tetrahedron Lett. 1985, 26, 131.
14. For theoretical treatments, see: Houk, K. N.; Paddon-Row, M. N.; Rordan, N. G.; Wu, Y. D.; Brown, F. K.; Spellmeyer, D. C.; Meta, J. T.; Li, Y.; Loucharich, R. J. Science 1985, 231, 1108. Kahn, S. D.; Hehre, W. S. J. Am. Chem. Soc. 1987, 109, 663.
15. Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 4127. Also see: Loncharich, R. J.; Brown, F. K.; Houk, K. N. J. Org. Chem. 1989, 54, 1129.
16. For some recent reviews, see: Pindur, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., Vol. 5, Chapter 4.1, pp 315-399. Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction; Wiley-Interscience: New York, 1990.
17. Schmid, H.; Grob, E. Helv. Chim. Ada 1949, 32, 77. Spath, E.; Schmid, H. Chem. Ber. 1940, 73, 243.