Catalytic Cyclopropanation of Alkenes via (2-Furyl)carbene Complexes from 1-Benzoyl-cis-1-buten-3-yne with Transition Metal Compounds

Journal of Organic Chemistry

Volumn 69, Issue 5, 2004, Pages 1557-1564

  Miki, Koji ^a   Yokoi, Tomomi ^a   Nishino, Fumiaki ^a   Kato, Yumiko ^a   Washitake, Yosuke ^a   Ohe, Kouichi ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; KETONES; TRANSITION METAL COMPOUNDS;

CARBENE ACCEPTOR; CYCLOPROPANATION;

OLEFINS;

(2 FURYL)CARBENE; 1 BENZOYL 1 BUTEN 3 YNE; ALKENE; CARBENE; CARBENOID; METAL COMPLEX; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COMPLEX FORMATION; CYCLOPROPANATION; DIMERIZATION; ISOMERISM; PHASE TRANSITION; REACTION ANALYSIS; SPECIES DIFFERENTIATION; STOICHIOMETRY; TECHNIQUE;

EID: 1442275531     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0352732     Document Type: Article

References (67)

1. (a) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules, 2nd ed.; University Science Books: Mill Valley CA, 1999; p 143.
2. (b) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, pp 421-468.
3. (c) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
4. (d) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
5. (e) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
6. Transition metal-catalyzed reorganization reaction of enynes. For example, [Pd] cat.: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636.
7. (b) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647.
8. (c) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850.
9. [Ru] cat.: (d) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049.
10. [Ru] or [Pt] cat.: (e) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N. ; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9140.
11. (f) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913.
12. [Pt] cat.: (g) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901.
13. (h) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704.
14. [Ir] cat.: (i) Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem 2001, 66, 4433.
15. The reactions of α,ω-enynes with dienes via cyclopropylcarbene complexes have been reported. See: (a) Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085.
16. (b) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183.
17. The reactions of α-ω-enynes with alcohols or alkynes with furans via cyclopropylcarbene complexes. See: (c) Méndez, M.; Muñoz, M. P.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 11549.
18. (d) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511.
19. (e) Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 67, 5197.
20. (f) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757.
21. Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310.
22. (a) Iwasawa, N.; Shido, M.; Kusama, H. J. Am. Chem. Soc. 2001, 123, 5814.
23. For an example of the azomethine ylide, see: (b) Kusama, H.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 11592.
24. Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650.
25. (a) Kimball, D. B.; Herges, R.; Haley, M. M. J. Am. Chem. Soc. 2002, 124, 1572.
26. (b) Kimball, D. B.; Weakley, T. J. R.; Herges, R.; Haley, M. M. J. Org. Chem. 2002, 67, 6395.
27. (c) Kimball, D. B.; Weakley, T. J. R.; Herges, R.; Haley, M. M. J. Am. Chem. Soc. 2002, 124, 13463.
28. (d) Kimball, D. B.; Haley, M. M. Angew. Chem., Int. Ed. 2002, 41, 3339.
29. (a) Rautenstrauch, V. Tetrahedron Lett. 1984, 25, 3845.
30. (b) Rautenstrauch, V. J. Org. Chem. 1984, 49, 950.
31. (c) Mainett, E.; Mouriès, V.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. Angew. Chem., Int. Ed. 2002, 41, 2132.
32. (d) Miki, K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 2003, 44, 2019.
33. (e) Miki, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2003, 68, 8505.
34. Oxidative rearrangement of propargyl esters by palladium catalyst has been reported, see: (f) Kataoka, H.; Watanabe, K.; Goto, K. Tetrahedron Lett. 1990, 31, 4181.
35. Ohe, K.; Miki, K.; Yokoi, T.; Nishino, F.; Uemura, S. Organometallics 2000, 19, 5525.
36. For benzopyranylidene complexes, see: Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226.
37. Ohe, K.; Yokoi, T.; Miki, K.; Nishino, F.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 526.
38. Miki, K.; Yokoi, T.; Nishino, F.; Ohe, K.; Uemura, S. J. Organomet. Chem. 2002, 645, 228.
39. For 6-endo-dig cyclization of 2-acylethynylbenzene with W(CO)5(THF) complex, see: Iwasawa, N.; Shido, M.; Kusama, H. J. Am. Chem. Soc. 2001, 123, 5814.
40. (a) Casey, C. P.; Polichnowski, S. W. J. Am. Chem. Soc. 1977, 99, 6097.
41. (b) Brookhart, M.; Nelson, G. O. J. Am. Chem. Soc. 1977, 99, 6099.
42. (c) Casey, C. P.; Polichnowski, S. W.; Shusterman, A. J.; Jones, C. R. J. Am. Chem. Soc. 1979, 101, 7282.
43. (d) Brookhart, M.; Humphrey, M. B.; Kratzer, H. J.; Nelson, G. O. J. Am. Chem. Soc. 1980, 102, 7802.
44. (e) Doyle, M. P.; Griffin, J. H.; Bagheri, V.; Dorow, R. L. Organometallics 1984, 3, 53.
45. (f) Fischer, H.; Zeuner, S.; Ackermann, K. J. Chem. Soc., Chem. Commun. 1984, 684.
46. (g) Fischer, H.; Hofmann, J. Chem. Ber. 1991, 124, 981.
47. (h) Casey, C. P.; Vosejpka, L. J. S Organometallics 1992,11, 738.
48. (i) Fischer, H.; Mauz, E.; Jaeger, M. J. Organomet. Chem. 1992, 427, 63.
49. (j) Jaeger, M.; Prosenc, M.-H.; Sontag, C.; Fischer, H. New J. Chem. 1995, 19, 911.
50. (a) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411.
51. (b) Helquist, P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, UK, 1991; Vol. 2, pp 143-194.
52. (c) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, UK, 1995; Vol. 12, pp 387-420.
53. Preliminary communication of catalytic cyclopropanation with ene-yne-carbonyl compounds. See: Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260.
54. (a) Hoffman, R. V.; Shechter, H. J. Am. Chem. Soc. 1971, 93, 5940.
55. (b) Hoffman, R. V.; Orphanides, G. G.; Shechter, H. J. Am. Chem. Soc. 1978, 100, 7927.
56. (c) Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 2000, 122, 8585.
57. The blue color indicates the generation of a (2-furyl)carbene chromium complex. Thus, consumption of the starting material 4 could be visibly monitored.
58. 5(THF), being in 10% and 32% yields, respectively, with a similar diastereoselectivity.
59. Catalytic approach for a 9-(9H-fluorenylidene)chromium complex, see: (a) Pfeiffer, J.; Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 2828.
60. (b) Pfeiffer, J.; Nieger, M.; Dötz, K. H. Eur. J. Org. Chem. 1998, 1011.
61. The structure was unambiguously determined by X-ray diffraction analysis of 9c. See the Supporting Information.
62. Furan ring construction from enyne-aldehyde derivatives with a stoichiometric amount of Fischer carbene complexes has been demonstrated. See: (a) Herndon, J. W.; Wang, H. J. Org. Chem. 1998, 63, 4564.
63. (b) Zhang, Y.; Herndon, J. W. J. Org. Chem. 2002, 67, 4177.
64. 2Cl in place of THF as solvent led to the rapid formation of the cyclopropanated product 10c in 96% yield in the reaction of styrene with 4c at room temperature for 1 h with a high trans selectivity (cis:trans = 11:89).
65. Lower yields of cyclopropanated products were due to the formation of either 1,2-difurylethene 12 in the Cr-catalyzed reaction or many unidentified products in the Pt-catalyzed reaction.
66. 2 as a carbenoid precursor, the ratio of cis:trans being 77:23. See ref 12e.
67. Kato, Y.; Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. Org. Lett. 2003, 5, 2619.