Rhodium(I)-catalyzed regioselective ring-expanding rearrangement of allenylcyclopropanes into methylenecyclopentenes

Angewandte Chemie - International Edition

Volumn 37, Issue 6, 1998, Pages 837-839

  Hayashi, Minoru ^a   Ohmatsu, Tadashi ^a   Meng, Yun Ping ^a   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Allenes; Carbocycles; Rearrangements; Rhodium; Small ring systems

Indexed keywords

EID: 0031900124     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980403)37:6<837::AID-ANIE837>3.0.CO;2-R     Document Type: Article

References (25)

1. Reviews: T. Hudlicky, J.W. Reed in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, pp. 899-970.
2. Examples of transition metal mediated vinylcyclopropane-cyclopentene rearrangements: a) V. Aris, J. M. Brown, J. A. Conneely, B. T. Golding, D. H. Williamson, J. Chem. Soc. Perkin Trans. 2 1975, 4-10; b) N. W. Alcock, J. M. Brown, J. A. Conneely, D. H. Williamson, ibid. 1975, 962-971; c) M. Murakami, S. Nishida, Chem. Lett. 1979, 927-930; d) T. Hudlicky, F. L. Koszyk, T. M. Kutchan, J. P. Sheth, J. Org. Chem. 1980, 45, 5020-5027; e) Y. Morizawa, K. Ohshima, H. Nozaki, Tetrahedron Lett. 1982, 23, 2871-2874.
3. Examples of transition metal mediated vinylcyclopropane-cyclopentene rearrangements: a) V. Aris, J. M. Brown, J. A. Conneely, B. T. Golding, D. H. Williamson, J. Chem. Soc. Perkin Trans. 2 1975, 4-10; b) N. W. Alcock, J. M. Brown, J. A. Conneely, D. H. Williamson, ibid. 1975, 962-971; c) M. Murakami, S. Nishida, Chem. Lett. 1979, 927-930; d) T. Hudlicky, F. L. Koszyk, T. M. Kutchan, J. P. Sheth, J. Org. Chem. 1980, 45, 5020-5027; e) Y. Morizawa, K. Ohshima, H. Nozaki, Tetrahedron Lett. 1982, 23, 2871-2874.
4. Examples of transition metal mediated vinylcyclopropane-cyclopentene rearrangements: a) V. Aris, J. M. Brown, J. A. Conneely, B. T. Golding, D. H. Williamson, J. Chem. Soc. Perkin Trans. 2 1975, 4-10; b) N. W. Alcock, J. M. Brown, J. A. Conneely, D. H. Williamson, ibid. 1975, 962-971; c) M. Murakami, S. Nishida, Chem. Lett. 1979, 927-930; d) T. Hudlicky, F. L. Koszyk, T. M. Kutchan, J. P. Sheth, J. Org. Chem. 1980, 45, 5020-5027; e) Y. Morizawa, K. Ohshima, H. Nozaki, Tetrahedron Lett. 1982, 23, 2871-2874.
5. Examples of transition metal mediated vinylcyclopropane-cyclopentene rearrangements: a) V. Aris, J. M. Brown, J. A. Conneely, B. T. Golding, D. H. Williamson, J. Chem. Soc. Perkin Trans. 2 1975, 4-10; b) N. W. Alcock, J. M. Brown, J. A. Conneely, D. H. Williamson, ibid. 1975, 962-971; c) M. Murakami, S. Nishida, Chem. Lett. 1979, 927-930; d) T. Hudlicky, F. L. Koszyk, T. M. Kutchan, J. P. Sheth, J. Org. Chem. 1980, 45, 5020-5027; e) Y. Morizawa, K. Ohshima, H. Nozaki, Tetrahedron Lett. 1982, 23, 2871-2874.
6. Examples of transition metal mediated vinylcyclopropane-cyclopentene rearrangements: a) V. Aris, J. M. Brown, J. A. Conneely, B. T. Golding, D. H. Williamson, J. Chem. Soc. Perkin Trans. 2 1975, 4-10; b) N. W. Alcock, J. M. Brown, J. A. Conneely, D. H. Williamson, ibid. 1975, 962-971; c) M. Murakami, S. Nishida, Chem. Lett. 1979, 927-930; d) T. Hudlicky, F. L. Koszyk, T. M. Kutchan, J. P. Sheth, J. Org. Chem. 1980, 45, 5020-5027; e) Y. Morizawa, K. Ohshima, H. Nozaki, Tetrahedron Lett. 1982, 23, 2871-2874.
7. a) T. Hudlicky, T. M. Kutchan, S. M. Naqvi, Org. React. 1985, 33, 247-335;
8. b) H. Hopf, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1997, Vol. E17c, pp. 2526-2537.
9. The pyrolysis of an allenylcyclopropane resulted in the formation of a mixture of five- and six-membered rings; no regioselectivity was observed for the cyclopropane ring cleavage: D.E. Minter, G. J. Fonken, Tetrahedron Lett. 1977, 18. 1717-1720.
10. There are a few reports dealing with the reactions of allenylcyclopropane derivatives: a) M. J. S. Dewar, G. J. Fonken, S. Kirschner, D. E. Minter, J. Am. Chem. Soc. 1975, 97, 6750-6753; b) W. R. Roth, T. Schmidt, H. Humbert, Chem. Ber. 1975, 108, 2171-2175; c) M. J. S. Dewar, G. J. Fonken, T. B. Jones, D. E. Minter, J. Chem. Soc. Perkin Trans. 2 1976, 764-767; d) D. E. Minter, G. J. Fonken, Tetrahedron Lett. 1977, 18, 4149-4152; e) D. E. Minter, G. J. Fonken, F. T. Cook, ibid. 1979, 20, 711-714; f) Z. Komiya, S. Nishida, J. Chem. Soc. Chem. Commun. 1982, 429-430; g) L. P. Olson, J. J. Gajewski, Tetrahedron Lett. 1993, 34, 2895-2898; h) N. Iwasawa, Y. Owada, T. Matsuo, Chem. Lett. 1995, 115-116.
11. There are a few reports dealing with the reactions of allenylcyclopropane derivatives: a) M. J. S. Dewar, G. J. Fonken, S. Kirschner, D. E. Minter, J. Am. Chem. Soc. 1975, 97, 6750-6753; b) W. R. Roth, T. Schmidt, H. Humbert, Chem. Ber. 1975, 108, 2171-2175; c) M. J. S. Dewar, G. J. Fonken, T. B. Jones, D. E. Minter, J. Chem. Soc. Perkin Trans. 2 1976, 764-767; d) D. E. Minter, G. J. Fonken, Tetrahedron Lett. 1977, 18, 4149-4152; e) D. E. Minter, G. J. Fonken, F. T. Cook, ibid. 1979, 20, 711-714; f) Z. Komiya, S. Nishida, J. Chem. Soc. Chem. Commun. 1982, 429-430; g) L. P. Olson, J. J. Gajewski, Tetrahedron Lett. 1993, 34, 2895-2898; h) N. Iwasawa, Y. Owada, T. Matsuo, Chem. Lett. 1995, 115-116.
12. There are a few reports dealing with the reactions of allenylcyclopropane derivatives: a) M. J. S. Dewar, G. J. Fonken, S. Kirschner, D. E. Minter, J. Am. Chem. Soc. 1975, 97, 6750-6753; b) W. R. Roth, T. Schmidt, H. Humbert, Chem. Ber. 1975, 108, 2171-2175; c) M. J. S. Dewar, G. J. Fonken, T. B. Jones, D. E. Minter, J. Chem. Soc. Perkin Trans. 2 1976, 764-767; d) D. E. Minter, G. J. Fonken, Tetrahedron Lett. 1977, 18, 4149-4152; e) D. E. Minter, G. J. Fonken, F. T. Cook, ibid. 1979, 20, 711-714; f) Z. Komiya, S. Nishida, J. Chem. Soc. Chem. Commun. 1982, 429-430; g) L. P. Olson, J. J. Gajewski, Tetrahedron Lett. 1993, 34, 2895-2898; h) N. Iwasawa, Y. Owada, T. Matsuo, Chem. Lett. 1995, 115-116.
13. There are a few reports dealing with the reactions of allenylcyclopropane derivatives: a) M. J. S. Dewar, G. J. Fonken, S. Kirschner, D. E. Minter, J. Am. Chem. Soc. 1975, 97, 6750-6753; b) W. R. Roth, T. Schmidt, H. Humbert, Chem. Ber. 1975, 108, 2171-2175; c) M. J. S. Dewar, G. J. Fonken, T. B. Jones, D. E. Minter, J. Chem. Soc. Perkin Trans. 2 1976, 764-767; d) D. E. Minter, G. J. Fonken, Tetrahedron Lett. 1977, 18, 4149-4152; e) D. E. Minter, G. J. Fonken, F. T. Cook, ibid. 1979, 20, 711-714; f) Z. Komiya, S. Nishida, J. Chem. Soc. Chem. Commun. 1982, 429-430; g) L. P. Olson, J. J. Gajewski, Tetrahedron Lett. 1993, 34, 2895-2898; h) N. Iwasawa, Y. Owada, T. Matsuo, Chem. Lett. 1995, 115-116.
14. There are a few reports dealing with the reactions of allenylcyclopropane derivatives: a) M. J. S. Dewar, G. J. Fonken, S. Kirschner, D. E. Minter, J. Am. Chem. Soc. 1975, 97, 6750-6753; b) W. R. Roth, T. Schmidt, H. Humbert, Chem. Ber. 1975, 108, 2171-2175; c) M. J. S. Dewar, G. J. Fonken, T. B. Jones, D. E. Minter, J. Chem. Soc. Perkin Trans. 2 1976, 764-767; d) D. E. Minter, G. J. Fonken, Tetrahedron Lett. 1977, 18, 4149-4152; e) D. E. Minter, G. J. Fonken, F. T. Cook, ibid. 1979, 20, 711-714; f) Z. Komiya, S. Nishida, J. Chem. Soc. Chem. Commun. 1982, 429-430; g) L. P. Olson, J. J. Gajewski, Tetrahedron Lett. 1993, 34, 2895-2898; h) N. Iwasawa, Y. Owada, T. Matsuo, Chem. Lett. 1995, 115-116.
15. There are a few reports dealing with the reactions of allenylcyclopropane derivatives: a) M. J. S. Dewar, G. J. Fonken, S. Kirschner, D. E. Minter, J. Am. Chem. Soc. 1975, 97, 6750-6753; b) W. R. Roth, T. Schmidt, H. Humbert, Chem. Ber. 1975, 108, 2171-2175; c) M. J. S. Dewar, G. J. Fonken, T. B. Jones, D. E. Minter, J. Chem. Soc. Perkin Trans. 2 1976, 764-767; d) D. E. Minter, G. J. Fonken, Tetrahedron Lett. 1977, 18, 4149-4152; e) D. E. Minter, G. J. Fonken, F. T. Cook, ibid. 1979, 20, 711-714; f) Z. Komiya, S. Nishida, J. Chem. Soc. Chem. Commun. 1982, 429-430; g) L. P. Olson, J. J. Gajewski, Tetrahedron Lett. 1993, 34, 2895-2898; h) N. Iwasawa, Y. Owada, T. Matsuo, Chem. Lett. 1995, 115-116.
16. There are a few reports dealing with the reactions of allenylcyclopropane derivatives: a) M. J. S. Dewar, G. J. Fonken, S. Kirschner, D. E. Minter, J. Am. Chem. Soc. 1975, 97, 6750-6753; b) W. R. Roth, T. Schmidt, H. Humbert, Chem. Ber. 1975, 108, 2171-2175; c) M. J. S. Dewar, G. J. Fonken, T. B. Jones, D. E. Minter, J. Chem. Soc. Perkin Trans. 2 1976, 764-767; d) D. E. Minter, G. J. Fonken, Tetrahedron Lett. 1977, 18, 4149-4152; e) D. E. Minter, G. J. Fonken, F. T. Cook, ibid. 1979, 20, 711-714; f) Z. Komiya, S. Nishida, J. Chem. Soc. Chem. Commun. 1982, 429-430; g) L. P. Olson, J. J. Gajewski, Tetrahedron Lett. 1993, 34, 2895-2898; h) N. Iwasawa, Y. Owada, T. Matsuo, Chem. Lett. 1995, 115-116.
17. There are a few reports dealing with the reactions of allenylcyclopropane derivatives: a) M. J. S. Dewar, G. J. Fonken, S. Kirschner, D. E. Minter, J. Am. Chem. Soc. 1975, 97, 6750-6753; b) W. R. Roth, T. Schmidt, H. Humbert, Chem. Ber. 1975, 108, 2171-2175; c) M. J. S. Dewar, G. J. Fonken, T. B. Jones, D. E. Minter, J. Chem. Soc. Perkin Trans. 2 1976, 764-767; d) D. E. Minter, G. J. Fonken, Tetrahedron Lett. 1977, 18, 4149-4152; e) D. E. Minter, G. J. Fonken, F. T. Cook, ibid. 1979, 20, 711-714; f) Z. Komiya, S. Nishida, J. Chem. Soc. Chem. Commun. 1982, 429-430; g) L. P. Olson, J. J. Gajewski, Tetrahedron Lett. 1993, 34, 2895-2898; h) N. Iwasawa, Y. Owada, T. Matsuo, Chem. Lett. 1995, 115-116.
18. P. A. Wender, H. Takahashi, B. Witulski, J. Am. Chem. Soc. 1995, 117, 4720-4721.
19. The structure of 3c was confirmed by X-ray crystallography on 5-isopropylidene-4-phenyl-1-cyclopentenylmethyl 3,5-dinitrobenzoate, obtained by reduction of 3c followed by esterification.
20. A trigonal-bipyramidal structure was determined for a rhodacycle obtained from Wilkinson's complex and a vinylallene: M. Murakami, K. Itam, Y. Ito, J. Am. Chem. Soc. 1996, 118, 11672-11673.
21. a) Z. Goldschmidt, B. Cramer, Chem. Soc. Rev. 1988, 17, 229-267;
22. b) R. I. Khusnutdinov, U. M. Dzhemilev, J. Organomet. Chem. 1994, 471, 1.
23. [2]
24. a) P. A. Pinke, R. D. Stauffer, R. G. Miller, J. Am. Chem. Soc. 1974, 96, 4229-4234;
25. b) R. G. Salomon, M. F. Salomon, J. L. C. Kachinski, ibid. 1977, 99, 1043-1054.