Nickel-Catalyzed Intramolecular [4 + 2] Dienyne Cycloadditions: An Efficient New Method for the Synthesis of Polycycles Containing Cyclohexa-1,4-dienes

Journal of the American Chemical Society

Volumn 111, Issue 16, 1989, Pages 6432-6434

  Wender, Paul A ^a   Jenkins, Thomas E ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845185652     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00198a071     Document Type: Article

References (9)

1. This limitation was initially treated by Sauer (Sauer, J. Angew. Chem., Int. Ed. Engl. 1966, 5, 211) and is reinforced in recent reviews on the Diels-Alder reaction: Ciganik, E. Org. React. 1984, 32, 1. Fallis, A. G. Can. J. Chem. 1984, 62, 183. Taber, D. F. Intramolecular Diels-Alder and Ene Reactions; Springer-Verlag: Berlin, 1984. Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63. The problems attending thermal dienyne cycloadditions have limited the number of examples of this process in synthesis. For some recent examples which provide calibration on the thermal requirements for such reactions, see: Shea, K. J.; Burke, L. D. J. Org. Chem. 1988, 53, 318. Kanematsu, K.; Hayakawa, K.; Yodo, M.; Ohsuki, S. J. Am. Chem. Soc. 1984, 106, 6735. Liu Z.-Y.; Zhou, X.-R.; Wu, Z.-M. J. Chem. Soc., Chem. Commun. 1987, 1868. Cyclization involving a deca-7,9-dien-1-yne was found to require 150 °C, 72 h, 89% (Trost, B. M. Stanford University, personal communication, 1988). Cyclizations involving nona-6,8-dien-1-ynes were found to require 150 °C, 5 h, 65-68% (Roush, W. R. Indiana University, personal communication, 1988).
2. For a general review, see: De Lucchi, O.; Modena, G. Tetrahedron 1984, 40, 2585. Recent examples of acetylene or general alkyne equivalents include the following: (trimethylsilyl)vinyl sulfone (Carr, R. C. V.; Paquette, L. A. J. Am. Chem. Soc. 1980, 102, 853), ethynyl sulfone (Davis, A. P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1980, 639), vinyl sulfoxide (Paquette, L. A.; Moerck, R. E.; Harirchian, B.; Magnus, P. D. J. Am. Chem. Soc. 1978, 100, 1597), (E)-or (Z)-1,2-bis(phenylsulfonyl)ethylene (De Lucchi, O.; Lucchini, V.; Pasquato, L.; Modena, G. J. Org. Chem. 1984, 49, 596), maleic anhydride (Westberg, H. H.; Dauben, H. J. Tetrahedron Lett. 1968, 5123) and 1,4-benzodithiin-1, 1,4,4-tetraoxide (Nakayama, J.; Nakamura, Y.; Hoshino, M. Heterocycles 1985, 23, 1119).
3. Mach, K.; Antropiusova, H.; Petrusova, L.; Turecek, F.; Hanus, V. J. Organomet. Chem. 1985, 289, 331.
4. tom Dieck, H.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778; Angew. Chem. Suppl. 1983, 1138. Carbonaro, A.; Greco, A.; Dall'Asta, G. J. Org. Chem. 1968, 33, 3948. Genet, J. P.; Ficini, J. Tetrahedron Lett. 1979, 17, 1499.
5. Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361.
6. For reviews and lead references, see: Wilke, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 185. Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: New York, 1982; Vol. 8, pp 613–797. Jolly, P. W.; Wilke, G. The Organic Chemistry of Nickel; Academic: New York, 1975; Vol. 2. Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. Wender, P. A.; Snapper, M. L. Tetrahedron Lett. 1987, 28, 2221. Dienyne cyclizations are being investigated by Professor Y. Ito and co-workers and will be reported in due course (Ito, Y., personal communication, May 1989).
7. Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904.
8. Ballester, P.; Costa, A.; Garcia-Raso, A.; Gomez-Solivellas, A.; Mestres, R. Tetrahedron Lett. 1985, 26, 3625.
9. Ihle, N. C. Ph.D. Dissertation, Stanford University, 1988.