Iridium-Catalyzed [5 + 1] Cycloaddition: Allenylcyclopropane as a Five-Carbon Assembling Unit

Journal of Organic Chemistry

Volumn 63, Issue 1, 1998, Pages 4-5

  Murakami, Masahiro ^a   Itami, Kenichiro ^a   Ubukata, Minoru ^a   Tsuji, Itaru ^a   Ito, Yoshihiko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002596809     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9718859     Document Type: Article

References (42)

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20. [4 + 1]: (a) Eaton, B. E.; Rollman, B.; Kaduk, J. A. J. Am. Chem. Soc. 1992, 124, 6245-6246. (b) Mandai, T.; Tsuji, J.; Tsujiguchi, Y. J. Am. Chem. Soc. 1993, 115, 5865-5866. (c) Sigman, M. S.; Eaton, B. E. J. Am. Chem. Soc. 1996, 118, 11783-11788. (d) Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synlett 1996, 218-220. (e) Murakami, M.; Itami, K; Ito, Y. J. Am. Chem. Soc, 1997, 119, 2950-2951. [4 + 2]: (f) Siegel, H.; Hopf, H.; Germer, A.; Binger, P. Chem. Ber. 1978, 111, 3112-3118. (g) Mandai, T.; Suzuki, S.; Ikawa, A.; Murakami, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1991, 32, 7687-7688. (h) Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 7163-7164.
21. [4 + 1]: (a) Eaton, B. E.; Rollman, B.; Kaduk, J. A. J. Am. Chem. Soc. 1992, 124, 6245-6246. (b) Mandai, T.; Tsuji, J.; Tsujiguchi, Y. J. Am. Chem. Soc. 1993, 115, 5865-5866. (c) Sigman, M. S.; Eaton, B. E. J. Am. Chem. Soc. 1996, 118, 11783-11788. (d) Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synlett 1996, 218-220. (e) Murakami, M.; Itami, K; Ito, Y. J. Am. Chem. Soc, 1997, 119, 2950-2951. [4 + 2]: (f) Siegel, H.; Hopf, H.; Germer, A.; Binger, P. Chem. Ber. 1978, 111, 3112-3118. (g) Mandai, T.; Suzuki, S.; Ikawa, A.; Murakami, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1991, 32, 7687-7688. (h) Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 7163-7164.
22. [4 + 1]: (a) Eaton, B. E.; Rollman, B.; Kaduk, J. A. J. Am. Chem. Soc. 1992, 124, 6245-6246. (b) Mandai, T.; Tsuji, J.; Tsujiguchi, Y. J. Am. Chem. Soc. 1993, 115, 5865-5866. (c) Sigman, M. S.; Eaton, B. E. J. Am. Chem. Soc. 1996, 118, 11783-11788. (d) Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synlett 1996, 218-220. (e) Murakami, M.; Itami, K; Ito, Y. J. Am. Chem. Soc, 1997, 119, 2950-2951. [4 + 2]: (f) Siegel, H.; Hopf, H.; Germer, A.; Binger, P. Chem. Ber. 1978, 111, 3112-3118. (g) Mandai, T.; Suzuki, S.; Ikawa, A.; Murakami, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1991, 32, 7687-7688. (h) Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 7163-7164.
23. [4 + 1]: (a) Eaton, B. E.; Rollman, B.; Kaduk, J. A. J. Am. Chem. Soc. 1992, 124, 6245-6246. (b) Mandai, T.; Tsuji, J.; Tsujiguchi, Y. J. Am. Chem. Soc. 1993, 115, 5865-5866. (c) Sigman, M. S.; Eaton, B. E. J. Am. Chem. Soc. 1996, 118, 11783-11788. (d) Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synlett 1996, 218-220. (e) Murakami, M.; Itami, K; Ito, Y. J. Am. Chem. Soc, 1997, 119, 2950-2951. [4 + 2]: (f) Siegel, H.; Hopf, H.; Germer, A.; Binger, P. Chem. Ber. 1978, 111, 3112-3118. (g) Mandai, T.; Suzuki, S.; Ikawa, A.; Murakami, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1991, 32, 7687-7688. (h) Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 7163-7164.
24. [4 + 1]: (a) Eaton, B. E.; Rollman, B.; Kaduk, J. A. J. Am. Chem. Soc. 1992, 124, 6245-6246. (b) Mandai, T.; Tsuji, J.; Tsujiguchi, Y. J. Am. Chem. Soc. 1993, 115, 5865-5866. (c) Sigman, M. S.; Eaton, B. E. J. Am. Chem. Soc. 1996, 118, 11783-11788. (d) Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synlett 1996, 218-220. (e) Murakami, M.; Itami, K; Ito, Y. J. Am. Chem. Soc, 1997, 119, 2950-2951. [4 + 2]: (f) Siegel, H.; Hopf, H.; Germer, A.; Binger, P. Chem. Ber. 1978, 111, 3112-3118. (g) Mandai, T.; Suzuki, S.; Ikawa, A.; Murakami, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1991, 32, 7687-7688. (h) Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 7163-7164.
25. [4 + 1]: (a) Eaton, B. E.; Rollman, B.; Kaduk, J. A. J. Am. Chem. Soc. 1992, 124, 6245-6246. (b) Mandai, T.; Tsuji, J.; Tsujiguchi, Y. J. Am. Chem. Soc. 1993, 115, 5865-5866. (c) Sigman, M. S.; Eaton, B. E. J. Am. Chem. Soc. 1996, 118, 11783-11788. (d) Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synlett 1996, 218-220. (e) Murakami, M.; Itami, K; Ito, Y. J. Am. Chem. Soc, 1997, 119, 2950-2951. [4 + 2]: (f) Siegel, H.; Hopf, H.; Germer, A.; Binger, P. Chem. Ber. 1978, 111, 3112-3118. (g) Mandai, T.; Suzuki, S.; Ikawa, A.; Murakami, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1991, 32, 7687-7688. (h) Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 7163-7164.
26. [4 + 1]: (a) Eaton, B. E.; Rollman, B.; Kaduk, J. A. J. Am. Chem. Soc. 1992, 124, 6245-6246. (b) Mandai, T.; Tsuji, J.; Tsujiguchi, Y. J. Am. Chem. Soc. 1993, 115, 5865-5866. (c) Sigman, M. S.; Eaton, B. E. J. Am. Chem. Soc. 1996, 118, 11783-11788. (d) Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synlett 1996, 218-220. (e) Murakami, M.; Itami, K; Ito, Y. J. Am. Chem. Soc, 1997, 119, 2950-2951. [4 + 2]: (f) Siegel, H.; Hopf, H.; Germer, A.; Binger, P. Chem. Ber. 1978, 111, 3112-3118. (g) Mandai, T.; Suzuki, S.; Ikawa, A.; Murakami, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1991, 32, 7687-7688. (h) Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 7163-7164.
27. For organic synthesis using functionalized cyclopropane derivatives, see: (a) Small Ring Compounds in Organic Synthesis I-IV. In Topics in Current Chemistry; de Meijere, A., Ed.; Springer: Berlin, 1986; Vol. 133; 1987; Vol. 135; 1988; Vol. 144; 1990; Vol. 155. (b) Carbocyclic Three- and Four-membered Ring Compounds. In Houben-Weyl. Methods of Organic Chemistry; de Meijere, A., Ed.; Thieme: Stuttgart, 1997; Vol. E17a-d.
28. For organic synthesis using functionalized cyclopropane derivatives, see: (a) Small Ring Compounds in Organic Synthesis I-IV. In Topics in Current Chemistry; de Meijere, A., Ed.; Springer: Berlin, 1986; Vol. 133; 1987; Vol. 135; 1988; Vol. 144; 1990; Vol. 155. (b) Carbocyclic Three- and Four-membered Ring Compounds. In Houben-Weyl. Methods of Organic Chemistry; de Meijere, A., Ed.; Thieme: Stuttgart, 1997; Vol. E17a-d.
29. For organic synthesis using functionalized cyclopropane derivatives, see: (a) Small Ring Compounds in Organic Synthesis I-IV. In Topics in Current Chemistry; de Meijere, A., Ed.; Springer: Berlin, 1986; Vol. 133; 1987; Vol. 135; 1988; Vol. 144; 1990; Vol. 155. (b) Carbocyclic Three- and Four-membered Ring Compounds. In Houben-Weyl. Methods of Organic Chemistry; de Meijere, A., Ed.; Thieme: Stuttgart, 1997; Vol. E17a-d.
30. For organic synthesis using functionalized cyclopropane derivatives, see: (a) Small Ring Compounds in Organic Synthesis I-IV. In Topics in Current Chemistry; de Meijere, A., Ed.; Springer: Berlin, 1986; Vol. 133; 1987; Vol. 135; 1988; Vol. 144; 1990; Vol. 155. (b) Carbocyclic Three- and Four-membered Ring Compounds. In Houben-Weyl. Methods of Organic Chemistry; de Meijere, A., Ed.; Thieme: Stuttgart, 1997; Vol. E17a-d.
31. For organic synthesis using functionalized cyclopropane derivatives, see: (a) Small Ring Compounds in Organic Synthesis I-IV. In Topics in Current Chemistry; de Meijere, A., Ed.; Springer: Berlin, 1986; Vol. 133; 1987; Vol. 135; 1988; Vol. 144; 1990; Vol. 155. (b) Carbocyclic Three- and Four-membered Ring Compounds. In Houben-Weyl. Methods of Organic Chemistry; de Meijere, A., Ed.; Thieme: Stuttgart, 1997; Vol. E17a-d.
32. Allenylcyclopropanes were prepared by the reactions of propargylic carbonates with cyclopropyl(cyano)thienylcuprates: Lipshutz, B. H.; Koerner, M.; Parker, D. A. Tetrahedron Lett. 1987, 28, 945-948. Details are available in the Supporting Information.
33. For transition metal-mediated skeletal isomerization of vinylcyclopropane, see: (a) Hudlicky, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 8, pp 899-970. (b) Khusnutdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1 -18 and references therein.
34. For transition metal-mediated skeletal isomerization of vinylcyclopropane, see: (a) Hudlicky, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 8, pp 899-970. (b) Khusnutdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1 -18 and references therein.
35. For thermal isomerization of allenylcyclopropane to methylenecyclopentene, see: (a) Roth, W. R.; Schmidt, T.; Humbert, H, Chem. Ber. 1975, 108, 2171-2175. (b) Minter, D. E.; Fonken, G. J. Tetrahedron Lett. 1977, 1717-1720. (c) Olson, L. P.; Gajewski, J. J. Tetrahedron Lett. 1993, 34, 2895-2898.
36. For thermal isomerization of allenylcyclopropane to methylenecyclopentene, see: (a) Roth, W. R.; Schmidt, T.; Humbert, H, Chem. Ber. 1975, 108, 2171-2175. (b) Minter, D. E.; Fonken, G. J. Tetrahedron Lett. 1977, 1717-1720. (c) Olson, L. P.; Gajewski, J. J. Tetrahedron Lett. 1993, 34, 2895-2898.
37. For thermal isomerization of allenylcyclopropane to methylenecyclopentene, see: (a) Roth, W. R.; Schmidt, T.; Humbert, H, Chem. Ber. 1975, 108, 2171-2175. (b) Minter, D. E.; Fonken, G. J. Tetrahedron Lett. 1977, 1717-1720. (c) Olson, L. P.; Gajewski, J. J. Tetrahedron Lett. 1993, 34, 2895-2898.
38. During the course of the present investigation, we became aware of the study on rhodium-catalyzed isomerization of allenylcyclopropane to methylenecyclopentene by Hayashi and Saigo: 72nd National Meeting of the Chemical Society of Japan; Tokyo, 1997.
39. 2 carbon atom.
40. 11d,12a-d,h
41. (a) Takeuchi, R.; Kashio, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 263-265.
42. (b) Chatani, N.; Yamaguchi, S.; Fukumoto, Y.; Murai, S. Organometallics 1995, 14, 4418-4420 and references therein.