Transition Metal Catalyzed [5 + 2] Cycloadditions of Vinylcyclopropanes and Alkynes: A Homolog of the Diels-Alder Reaction for the Synthesis of Seven-Membered Rings

Journal of the American Chemical Society

Volumn 117, Issue 16, 1995, Pages 4720-4721

  Wender, Paul A ^a   Takahashi, Hisashi ^a   Witulski, Bernhard ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; CYCLOPROPANE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0028956752     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00121a036     Document Type: Article

References (5)

1. For examples, see: Sarel, S.; Breuer, E. J. Am. Chem. Soc. 1959, 81, 6522. Sarel, S.; Felzenstein, A.; Yovell, J. J. Chem. Soc., Chem. Commun. 1973, 859. Sarel, S.; Felzenstein, A.; Yovell, J. J. Chem. Soc., Chem. Commun. 1974, 753. Felzenstein, A.; Sarel, S.; Yovell, J. J. Chem. Soc., Chem. Commun. 1975, 918.
2. Related work includes the following: Effenberger, F.; Podszun, W. Angew. Chem., Int. Ed. Engl. 1969, 8, 976. Nishida, S.; Moritani, I.; Teraji, T. J. Chem. Soc., Chem. Commun. 1970, 501. Baldwin, J. E.; Pinschmidt, R. K. Tetrahedron Lett. 1971, 935. Shimizu, N.; Fujioka, T.; Ishizuka, S.-I.; Tsuji, T.; Nishida, S. J. Am. Chem. Soc. 1977, 99, 5972. Christl, M.; Brunn, E.; Lanzendörfer, F. J. Am. Chem. Soc. 1984, 106, 373.
3. For representative examples, see: Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. Wender, P. A.; Ihle, N. C. Tetrahedron Lett. 1987, 28, 2451. Wender, P. A.; Snapper, M. L. Tetrahedron Lett. 1987, 28, 2221. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904. Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843.
4. There are only three possible two-component cycloadditions that lead to seven-membered rings: [6 + 1], [5 + 2], and [4 + 3]. For examples and lead references, see the following. [6 + 1] (in the form of carbene insertions into arenes): Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. [5 + 2]: Sánchez, I. H.; Yáñez, R.; Enríquez, R.; Joseph-Nathan, P. J. Org. Chem. 1981, 46, 2818. Sammes, P. G. Gazz. Chim. Ital. 1986, 116, 109. Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954. Padwa, A.; Hombuckel, S. F.; Fryxell, G. E.; Stull, P. D. J. Org. Chem. 1992, 57, 5747. Wender, P. A.; Siggel, L.; Nuss, J. M. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, pp 645–673. [4 + 3]: Noyori, R. Acc. Chem. Res. 1979, 12, 61. Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. Mann, J. Tetrahedron 1986, 42, 4611. Harmata, M.; Elahmad, S. Tetrahedron Lett. 1993, 34, 789. Giguere, R. J.; Tassely, S. M.; Rose, M. I.; Krishnamurthy, V. V. Tetrahedron Lett. 1990, 31, 4577. Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. Trost, B. M.; Schneider, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 213. Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. Davies, H. M. L. Tetrahedron 1993, 49, 5203. Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, pp 593–615. Boger, D. L.; Brotherton, C. E. J. Org. Chem. 1985, 50, 3425.
5. For reviews and lead references on metal-mediated cleavage of cyclopropanes, see: Sarel, S. Acc. Chem. Res. 1978, 11, 204. Khusnutdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1. Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, pp 899—970. Goldschmidt, Z.; Crammer, B. Chem. Soc. Rev. 1988, 17, 229. Moriarty, R. M.; Yeh, L. L.; Ramey, K. C. J. Am. Chem. Soc. 1971, 93, 6709. Powell, K. G.; McQuillin, F. S. J. Chem. Soc., Chem. Commun. 1971, 931. Aumann, R. J. Am. Chem. Soc. 1974, 96, 2631. Russell, R. K.; Wingard, R. E.; Paquette, L. A. J. Am. Chem. Soc. 1974, 96, 7483. Pinke, P. A.; Stauffer, R. D.; Miller, R. G. J. Am. Chem. Soc. 1974, 96, 4229. Eilbracht, P. Chem. Ber. 1976, 109, 1429, 3136. Salomon, M. F.; Salomon, R. G.; Kachinski, L. C. J. Am. Chem. Soc. 1977, 99, 1043. Scharf, H. D.; Mattay, J. Tetrahedron Lett. 1977, 401. Alcock, N. W.; Brown, J. M.; Conneely, J. A.; Williamson, D. H. J. Chem. Soc., Perkin Trans. 2 1979, 962. Murakami, M.; Nishida, S. Chem. Lett. 1979, 927. Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. J. Org. Chem. 1980, 45, 5020. Doyle, M. P.; van Leusen, D. J. Am. Chem. Soc. 1981, 103, 5917. Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 2871. Binger, P.; Brinkmann, A.; Wedernann, P. Chem. Ber. 1983, 116, 2920. Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2315, 2326. Larock, R. C.; Varaprath, S. J. Org. Chem. 1984, 49, 3432. Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. Fourner, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. Turner, S. U.; Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1992, 114, 8394. Huffman, M. A.; Liebeskind, L. S. J. Am. Chem. Soc. 1993, 115, 4895. Herndon, J. W.; Turner, S. U.; McMullen, L. A.; Matasi, J. J.; Schattner, W. F. K. Adv. Metalorg. Chem. 1994, 3, 51. Dimmock, P. W.; Whitby, J. J. Chem. Soc., Chem. Commun. 1994, 2323. Hanzawa, Y.; Harada, S.; Nishio, R.; Taguchi, T. Tetrahedron Lett. 1994, 35, 9421. Ryu, I.; Ikura, K.; Tamura, Y.; Maenaka, J.; Ogawa, A.; Sonoda, N. Synlett 1994, 941. Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153.