Versatile Reactivities of Carbonyl Ylids toward Unactivated Alkenes and Heterodipolarophiles, and their Synthetic Use

Synlett

Volumn 1996, Issue 3, 1996, Pages 234-236

  Hojo, Makoto ^a   Ishibashi, Naruyasu ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

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Indexed keywords

EID: 1542740683     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5396     Document Type: Article

References (39)

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11. Griffin reported that the color indicating the existence of the carbonyl ylid rapidly faded in the presence of norbornadiene, but did not detect the cycloadducts. Later, Lee also reported that the corresponding cycloadduct was not detected in the reaction of diphenyl-carbonyl ylid with norbornene. T. Do-Minh, A. M. Trozzolo, G. W. Griffin, J. Am. Chem. Soc. 1970, 92, 1402-1403; G. A. Lee, J. Org. Chem. 1976, 41, 2656-2658; A. Albini, D. R. Arnold, Can. J. Chem. 1978, 56, 2985-2993.
12. Griffin reported that the color indicating the existence of the carbonyl ylid rapidly faded in the presence of norbornadiene, but did not detect the cycloadducts. Later, Lee also reported that the corresponding cycloadduct was not detected in the reaction of diphenyl-carbonyl ylid with norbornene. T. Do-Minh, A. M. Trozzolo, G. W. Griffin, J. Am. Chem. Soc. 1970, 92, 1402-1403; G. A. Lee, J. Org. Chem. 1976, 41, 2656-2658; A. Albini, D. R. Arnold, Can. J. Chem. 1978, 56, 2985-2993.
13. Griffin reported that the color indicating the existence of the carbonyl ylid rapidly faded in the presence of norbornadiene, but did not detect the cycloadducts. Later, Lee also reported that the corresponding cycloadduct was not detected in the reaction of diphenyl-carbonyl ylid with norbornene. T. Do-Minh, A. M. Trozzolo, G. W. Griffin, J. Am. Chem. Soc. 1970, 92, 1402-1403; G. A. Lee, J. Org. Chem. 1976, 41, 2656-2658; A. Albini, D. R. Arnold, Can. J. Chem. 1978, 56, 2985-2993.
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15. W. R. Dolbier Jr., S. H. Dai, Tetrahedron Lett. 1970, 4645-4646; H. Hamberger, R. Huisgen, J. Chem. Soc., Chem. Commun. 1971, 1190-1192; A. Dahmen, H. Hamberger, R. Huisgen, V. Markowski, ibid. 1971, 1192-1194.
16. W. R. Dolbier Jr., S. H. Dai, Tetrahedron Lett. 1970, 4645-4646; H. Hamberger, R. Huisgen, J. Chem. Soc., Chem. Commun. 1971, 1190-1192; A. Dahmen, H. Hamberger, R. Huisgen, V. Markowski, ibid. 1971, 1192-1194.
17. P. Rajagopalan, B. G. Advani, Tetrahedron Lett. 1967, 2689-2695; R. W. Hoffmann, H. J. Luthardt, Chem. Ber. 1968, 101, 3861-3871.
18. P. Rajagopalan, B. G. Advani, Tetrahedron Lett. 1967, 2689-2695; R. W. Hoffmann, H. J. Luthardt, Chem. Ber. 1968, 101, 3861-3871.
19. Huisgen found some electron-deficient alkenes react with carbonyl ylids faster than aldehydes used for the generation of the carbonyl ylids. P. March, R. Huisgen, J. Am. Chem. Soc. 1982, 104, 4952; R. Huisgen, P. March, ibid. 1982, 104, 4953-4954; H. S. Gill, J. A. Landgrebe, J. Org. Chem. 1983, 48, 1051-1055; J. F. Gisch, J. A. Landgrebe, ibid. 1985, 50, 2050-2054; T. Ibata, M. T. H. Liu, J. Toyoda, Tetrahedron Lett. 1986, 27, 4383-4386; T. Ibata, J. Toyoda, M. T. H. Liu, Chem. Lett. 1987, 2135-2138; M. T. H. Liu, N. Soundararajan, S. M. Anand, T. Ibata, Tetrahedron Lett. 1987, 28, 1011-1014; R. P. L'Esperance, T. M. Ford, M. Jones, Jr. J. Am. Chem. Soc. 1988, 110, 209-213; R. Bonneau, M. T. H. Liu, ibid. 1990, 112, 744-747.
20. Huisgen found some electron-deficient alkenes react with carbonyl ylids faster than aldehydes used for the generation of the carbonyl ylids. P. March, R. Huisgen, J. Am. Chem. Soc. 1982, 104, 4952; R. Huisgen, P. March, ibid. 1982, 104, 4953-4954; H. S. Gill, J. A. Landgrebe, J. Org. Chem. 1983, 48, 1051-1055; J. F. Gisch, J. A. Landgrebe, ibid. 1985, 50, 2050-2054; T. Ibata, M. T. H. Liu, J. Toyoda, Tetrahedron Lett. 1986, 27, 4383-4386; T. Ibata, J. Toyoda, M. T. H. Liu, Chem. Lett. 1987, 2135-2138; M. T. H. Liu, N. Soundararajan, S. M. Anand, T. Ibata, Tetrahedron Lett. 1987, 28, 1011-1014; R. P. L'Esperance, T. M. Ford, M. Jones, Jr. J. Am. Chem. Soc. 1988, 110, 209-213; R. Bonneau, M. T. H. Liu, ibid. 1990, 112, 744-747.
21. Huisgen found some electron-deficient alkenes react with carbonyl ylids faster than aldehydes used for the generation of the carbonyl ylids. P. March, R. Huisgen, J. Am. Chem. Soc. 1982, 104, 4952; R. Huisgen, P. March, ibid. 1982, 104, 4953-4954; H. S. Gill, J. A. Landgrebe, J. Org. Chem. 1983, 48, 1051-1055; J. F. Gisch, J. A. Landgrebe, ibid. 1985, 50, 2050-2054; T. Ibata, M. T. H. Liu, J. Toyoda, Tetrahedron Lett. 1986, 27, 4383-4386; T. Ibata, J. Toyoda, M. T. H. Liu, Chem. Lett. 1987, 2135-2138; M. T. H. Liu, N. Soundararajan, S. M. Anand, T. Ibata, Tetrahedron Lett. 1987, 28, 1011-1014; R. P. L'Esperance, T. M. Ford, M. Jones, Jr. J. Am. Chem. Soc. 1988, 110, 209-213; R. Bonneau, M. T. H. Liu, ibid. 1990, 112, 744-747.
22. Huisgen found some electron-deficient alkenes react with carbonyl ylids faster than aldehydes used for the generation of the carbonyl ylids. P. March, R. Huisgen, J. Am. Chem. Soc. 1982, 104, 4952; R. Huisgen, P. March, ibid. 1982, 104, 4953-4954; H. S. Gill, J. A. Landgrebe, J. Org. Chem. 1983, 48, 1051-1055; J. F. Gisch, J. A. Landgrebe, ibid. 1985, 50, 2050-2054; T. Ibata, M. T. H. Liu, J. Toyoda, Tetrahedron Lett. 1986, 27, 4383-4386; T. Ibata, J. Toyoda, M. T. H. Liu, Chem. Lett. 1987, 2135-2138; M. T. H. Liu, N. Soundararajan, S. M. Anand, T. Ibata, Tetrahedron Lett. 1987, 28, 1011-1014; R. P. L'Esperance, T. M. Ford, M. Jones, Jr. J. Am. Chem. Soc. 1988, 110, 209-213; R. Bonneau, M. T. H. Liu, ibid. 1990, 112, 744-747.
23. Huisgen found some electron-deficient alkenes react with carbonyl ylids faster than aldehydes used for the generation of the carbonyl ylids. P. March, R. Huisgen, J. Am. Chem. Soc. 1982, 104, 4952; R. Huisgen, P. March, ibid. 1982, 104, 4953-4954; H. S. Gill, J. A. Landgrebe, J. Org. Chem. 1983, 48, 1051-1055; J. F. Gisch, J. A. Landgrebe, ibid. 1985, 50, 2050-2054; T. Ibata, M. T. H. Liu, J. Toyoda, Tetrahedron Lett. 1986, 27, 4383-4386; T. Ibata, J. Toyoda, M. T. H. Liu, Chem. Lett. 1987, 2135-2138; M. T. H. Liu, N. Soundararajan, S. M. Anand, T. Ibata, Tetrahedron Lett. 1987, 28, 1011-1014; R. P. L'Esperance, T. M. Ford, M. Jones, Jr. J. Am. Chem. Soc. 1988, 110, 209-213; R. Bonneau, M. T. H. Liu, ibid. 1990, 112, 744-747.
24. Huisgen found some electron-deficient alkenes react with carbonyl ylids faster than aldehydes used for the generation of the carbonyl ylids. P. March, R. Huisgen, J. Am. Chem. Soc. 1982, 104, 4952; R. Huisgen, P. March, ibid. 1982, 104, 4953-4954; H. S. Gill, J. A. Landgrebe, J. Org. Chem. 1983, 48, 1051-1055; J. F. Gisch, J. A. Landgrebe, ibid. 1985, 50, 2050-2054; T. Ibata, M. T. H. Liu, J. Toyoda, Tetrahedron Lett. 1986, 27, 4383-4386; T. Ibata, J. Toyoda, M. T. H. Liu, Chem. Lett. 1987, 2135-2138; M. T. H. Liu, N. Soundararajan, S. M. Anand, T. Ibata, Tetrahedron Lett. 1987, 28, 1011-1014; R. P. L'Esperance, T. M. Ford, M. Jones, Jr. J. Am. Chem. Soc. 1988, 110, 209-213; R. Bonneau, M. T. H. Liu, ibid. 1990, 112, 744-747.
25. Huisgen found some electron-deficient alkenes react with carbonyl ylids faster than aldehydes used for the generation of the carbonyl ylids. P. March, R. Huisgen, J. Am. Chem. Soc. 1982, 104, 4952; R. Huisgen, P. March, ibid. 1982, 104, 4953-4954; H. S. Gill, J. A. Landgrebe, J. Org. Chem. 1983, 48, 1051-1055; J. F. Gisch, J. A. Landgrebe, ibid. 1985, 50, 2050-2054; T. Ibata, M. T. H. Liu, J. Toyoda, Tetrahedron Lett. 1986, 27, 4383-4386; T. Ibata, J. Toyoda, M. T. H. Liu, Chem. Lett. 1987, 2135-2138; M. T. H. Liu, N. Soundararajan, S. M. Anand, T. Ibata, Tetrahedron Lett. 1987, 28, 1011-1014; R. P. L'Esperance, T. M. Ford, M. Jones, Jr. J. Am. Chem. Soc. 1988, 110, 209-213; R. Bonneau, M. T. H. Liu, ibid. 1990, 112, 744-747.
26. Huisgen found some electron-deficient alkenes react with carbonyl ylids faster than aldehydes used for the generation of the carbonyl ylids. P. March, R. Huisgen, J. Am. Chem. Soc. 1982, 104, 4952; R. Huisgen, P. March, ibid. 1982, 104, 4953-4954; H. S. Gill, J. A. Landgrebe, J. Org. Chem. 1983, 48, 1051-1055; J. F. Gisch, J. A. Landgrebe, ibid. 1985, 50, 2050-2054; T. Ibata, M. T. H. Liu, J. Toyoda, Tetrahedron Lett. 1986, 27, 4383-4386; T. Ibata, J. Toyoda, M. T. H. Liu, Chem. Lett. 1987, 2135-2138; M. T. H. Liu, N. Soundararajan, S. M. Anand, T. Ibata, Tetrahedron Lett. 1987, 28, 1011-1014; R. P. L'Esperance, T. M. Ford, M. Jones, Jr. J. Am. Chem. Soc. 1988, 110, 209-213; R. Bonneau, M. T. H. Liu, ibid. 1990, 112, 744-747.
27. Huisgen found some electron-deficient alkenes react with carbonyl ylids faster than aldehydes used for the generation of the carbonyl ylids. P. March, R. Huisgen, J. Am. Chem. Soc. 1982, 104, 4952; R. Huisgen, P. March, ibid. 1982, 104, 4953-4954; H. S. Gill, J. A. Landgrebe, J. Org. Chem. 1983, 48, 1051-1055; J. F. Gisch, J. A. Landgrebe, ibid. 1985, 50, 2050-2054; T. Ibata, M. T. H. Liu, J. Toyoda, Tetrahedron Lett. 1986, 27, 4383-4386; T. Ibata, J. Toyoda, M. T. H. Liu, Chem. Lett. 1987, 2135-2138; M. T. H. Liu, N. Soundararajan, S. M. Anand, T. Ibata, Tetrahedron Lett. 1987, 28, 1011-1014; R. P. L'Esperance, T. M. Ford, M. Jones, Jr. J. Am. Chem. Soc. 1988, 110, 209-213; R. Bonneau, M. T. H. Liu, ibid. 1990, 112, 744-747.
28. K. N. Houk, N. G. Rondan, C. Santiago, C. J. Gallo, R. W. Gandour, G. W. Griffin, J. Am. Chem. Soc. 1980, 102, 1504-1512.
29. M. Hojo, M. Ohkuma, N. Ishibashi, A. Hosomi, Tetrahedron Lett. 1993, 34, 5943-5946.
30. A. Hosomi, Y. Sakata, H. Sakurai, Chem. Lett. 1984 1117-1120; A. Hosomi, Y. Miyashiro, R. Yoshida, Y. Tominaga, T. Yanagi, M. Hojo, J. Org. Chem. 1990, 55, 5308-5310; Y. Tominaga, K. Ogata, S. Kohra, M. Hojo, A. Hosomi, Tetrahedron Lett. 1991, 32, 5987-5990. For reviews in this area, see, Y. Tominaga, M. Hojo, A. Hosomi, J. Synth. Org. Chem., Japan 1992, 50, 48-60; E. Vedejs, F. G. West, Chem. Revs. 1986, 86, 941-955.
31. A. Hosomi, Y. Sakata, H. Sakurai, Chem. Lett. 1984 1117-1120; A. Hosomi, Y. Miyashiro, R. Yoshida, Y. Tominaga, T. Yanagi, M. Hojo, J. Org. Chem. 1990, 55, 5308-5310; Y. Tominaga, K. Ogata, S. Kohra, M. Hojo, A. Hosomi, Tetrahedron Lett. 1991, 32, 5987-5990. For reviews in this area, see, Y. Tominaga, M. Hojo, A. Hosomi, J. Synth. Org. Chem., Japan 1992, 50, 48-60; E. Vedejs, F. G. West, Chem. Revs. 1986, 86, 941-955.
32. A. Hosomi, Y. Sakata, H. Sakurai, Chem. Lett. 1984 1117-1120; A. Hosomi, Y. Miyashiro, R. Yoshida, Y. Tominaga, T. Yanagi, M. Hojo, J. Org. Chem. 1990, 55, 5308-5310; Y. Tominaga, K. Ogata, S. Kohra, M. Hojo, A. Hosomi, Tetrahedron Lett. 1991, 32, 5987-5990. For reviews in this area, see, Y. Tominaga, M. Hojo, A. Hosomi, J. Synth. Org. Chem., Japan 1992, 50, 48-60; E. Vedejs, F. G. West, Chem. Revs. 1986, 86, 941-955.
33. A. Hosomi, Y. Sakata, H. Sakurai, Chem. Lett. 1984 1117-1120; A. Hosomi, Y. Miyashiro, R. Yoshida, Y. Tominaga, T. Yanagi, M. Hojo, J. Org. Chem. 1990, 55, 5308-5310; Y. Tominaga, K. Ogata, S. Kohra, M. Hojo, A. Hosomi, Tetrahedron Lett. 1991, 32, 5987-5990. For reviews in this area, see, Y. Tominaga, M. Hojo, A. Hosomi, J. Synth. Org. Chem., Japan 1992, 50, 48-60; E. Vedejs, F. G. West, Chem. Revs. 1986, 86, 941-955.
34. A. Hosomi, Y. Sakata, H. Sakurai, Chem. Lett. 1984 1117-1120; A. Hosomi, Y. Miyashiro, R. Yoshida, Y. Tominaga, T. Yanagi, M. Hojo, J. Org. Chem. 1990, 55, 5308-5310; Y. Tominaga, K. Ogata, S. Kohra, M. Hojo, A. Hosomi, Tetrahedron Lett. 1991, 32, 5987-5990. For reviews in this area, see, Y. Tominaga, M. Hojo, A. Hosomi, J. Synth. Org. Chem., Japan 1992, 50, 48-60; E. Vedejs, F. G. West, Chem. Revs. 1986, 86, 941-955.
35. E. Laborde, Tetrahedron Lett. 1992, 33, 6607-6610.
36. 10
37. Experimental procedure: A two-necked round bottom flask containing a stirring bar and cesium fluoride (1.2 mmol) was heated by an oil bath (90-110°C) under reduced pressure for 1 h. After drying, the flask was purged with argon and dry acetonitrile (2.5 ml), a dipolarophile (2.0 mmol), and chloromethyl silylmethyl ether 1 (1.0 mmol) were successively introduced to the flask. After stirring the mixture for 5 h at room temperature, a solution of saturated sodium hydrogen carbonate was added to the mixture. Extraction with ether, drying over sodium sulfate, and evaporation gave a crude product. The product was purified by column chromatography.
38. All of the results in regioselectivities obtained in this work are well correlated with orbital coefficients in the calculation. AM1 calculation concerning [3+2] cycloaddition of carbonyl ylids with various dipolarophiles will be reported later in details. M. Hojo, N. Ishibashi, T. Kizaki, O. Takahashi, O. Kikuchi, A. Hosomi, to be published.
39. A. Pelter, R. S. Ward, D. J. Watson, P. Collins, I. T. Kay, J. Chem. Soc. Perkin 1 1982 175-181.