Ruthenium carbonyl-catalyzed [2 + 2 + 1]-cycloaddition of ketones, olefins, and carbon monoxide, leading to functionalized γ-butyrolactones [6]

Journal of the American Chemical Society

Volumn 121, Issue 30, 1999, Pages 7160-7161

  Chatani, Naoto ^a   Tobisu, Mamoru ^a   Asaumi, Taku ^a   Fukumoto, Yoshiya ^a   Murai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CARBON MONOXIDE; CARBONYL DERIVATIVE; KETONE DERIVATIVE; LACTONE DERIVATIVE; RUTHENIUM COMPLEX;

CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; LETTER; POLYMERIZATION;

EID: 0033523213     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991223w     Document Type: Letter

References (24)

1. For reviews on transition-metal-catalyzed cycloaddition reactions, see: Schore, N. E. Chem. Rev. 1988, 88, 1081. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
2. For reviews on transition-metal-catalyzed cycloaddition reactions, see: Schore, N. E. Chem. Rev. 1988, 88, 1081. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
3. For reviews on transition-metal-catalyzed cycloaddition reactions, see: Schore, N. E. Chem. Rev. 1988, 88, 1081. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
4. For recent papers on [2 + 2 + 1] cycloaddition reactions using CO, see: Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. For a recent paper on [4 + 1] cycloaddition reactions using CO, see: Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. Murakami, M.; Itami, K.; Ko, Y. J. Am. Chem. Soc. 1999, 121, 4130. For a recent paper on [4 + 4 + 1] cycloaddition reactions using CO, see: Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 3418.
5. For recent papers on [2 + 2 + 1] cycloaddition reactions using CO, see: Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. For a recent paper on [4 + 1] cycloaddition reactions using CO, see: Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. Murakami, M.; Itami, K.; Ko, Y. J. Am. Chem. Soc. 1999, 121, 4130. For a recent paper on [4 + 4 + 1] cycloaddition reactions using CO, see: Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 3418.
6. For recent papers on [2 + 2 + 1] cycloaddition reactions using CO, see: Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. For a recent paper on [4 + 1] cycloaddition reactions using CO, see: Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. Murakami, M.; Itami, K.; Ko, Y. J. Am. Chem. Soc. 1999, 121, 4130. For a recent paper on [4 + 4 + 1] cycloaddition reactions using CO, see: Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 3418.
7. For recent papers on [2 + 2 + 1] cycloaddition reactions using CO, see: Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. For a recent paper on [4 + 1] cycloaddition reactions using CO, see: Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. Murakami, M.; Itami, K.; Ko, Y. J. Am. Chem. Soc. 1999, 121, 4130. For a recent paper on [4 + 4 + 1] cycloaddition reactions using CO, see: Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 3418.
8. For recent papers on [2 + 2 + 1] cycloaddition reactions using CO, see: Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. For a recent paper on [4 + 1] cycloaddition reactions using CO, see: Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. Murakami, M.; Itami, K.; Ko, Y. J. Am. Chem. Soc. 1999, 121, 4130. For a recent paper on [4 + 4 + 1] cycloaddition reactions using CO, see: Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 3418.
9. For recent papers on [2 + 2 + 1] cycloaddition reactions using CO, see: Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. For a recent paper on [4 + 1] cycloaddition reactions using CO, see: Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. Murakami, M.; Itami, K.; Ko, Y. J. Am. Chem. Soc. 1999, 121, 4130. For a recent paper on [4 + 4 + 1] cycloaddition reactions using CO, see: Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 3418.
10. For recent papers on [2 + 2 + 1] cycloaddition reactions using CO, see: Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. For a recent paper on [4 + 1] cycloaddition reactions using CO, see: Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. Murakami, M.; Itami, K.; Ko, Y. J. Am. Chem. Soc. 1999, 121, 4130. For a recent paper on [4 + 4 + 1] cycloaddition reactions using CO, see: Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 3418.
11. For recent papers on [2 + 2 + 1] cycloaddition reactions using CO, see: Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. For a recent paper on [4 + 1] cycloaddition reactions using CO, see: Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. Murakami, M.; Itami, K.; Ko, Y. J. Am. Chem. Soc. 1999, 121, 4130. For a recent paper on [4 + 4 + 1] cycloaddition reactions using CO, see: Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 3418.
12. γ-Butyrolactones are important precursors for the preparation of α-methylene- γ-bulyrolactones or butenolides which are found in the skeleton of various natural products. For reviews, see: Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94. Petragnani, N.; Ferraz, H. M. C.; Suva, G. V. J. Syntheis 1986, 157. Ito, M. Pure Appl. Chem. 1991, 63, 13.
13. γ-Butyrolactones are important precursors for the preparation of α-methylene- γ-bulyrolactones or butenolides which are found in the skeleton of various natural products. For reviews, see: Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94. Petragnani, N.; Ferraz, H. M. C.; Suva, G. V. J. Syntheis 1986, 157. Ito, M. Pure Appl. Chem. 1991, 63, 13.
14. γ-Butyrolactones are important precursors for the preparation of α-methylene- γ-bulyrolactones or butenolides which are found in the skeleton of various natural products. For reviews, see: Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94. Petragnani, N.; Ferraz, H. M. C.; Suva, G. V. J. Syntheis 1986, 157. Ito, M. Pure Appl. Chem. 1991, 63, 13.
15. Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557.
16. Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818. Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 4424.
17. Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818. Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 4424.
18. All new compounds were characterized by NMR, IR, mass spectral data, and by elemental analyses or high-resolution mass spectra. See Supporting Information.
19. Beers, O. C. P.; Bouman, M. M.; Elsevier: C. J.; Smeets, W. J. J.; Spek, A. L. Inorg. Chem. 1993, 32, 3015.
20. 3 (X = O or N), which underwent the coupling reaction with acetyelenes (or olefins) and CO. See also refs 9 and 10.
21. 3(butenolide) complexes. A similar reaction route to 20 → 23 was proposed: van Wijnkoop, M.; Siebenlist, R.; de Lange, P. P. M.; Frühauf, H.-W.; Vieze, K.; Smeets, W. J. J.; Spek, A. L. Organometallics 1993, 12, 4172, van Wijnkoop, M.; Siebenlist,R.; Ernsting, J. M.; de Lange, P. P. M.; Frühauf, H.-W.; Horn, E.; Spek, A. L. J. Organomet. Chem. 1994, 482, 99.
22. 3(butenolide) complexes. A similar reaction route to 20 → 23 was proposed: van Wijnkoop, M.; Siebenlist, R.; de Lange, P. P. M.; Frühauf, H.-W.; Vieze, K.; Smeets, W. J. J.; Spek, A. L. Organometallics 1993, 12, 4172, van Wijnkoop, M.; Siebenlist, R.; Ernsting, J. M.; de Lange, P. P. M.; Frühauf, H.-W.; Horn, E.; Spek, A. L. J. Organomet. Chem. 1994, 482, 99.
23. 3 with dimethyl maleate or dimethyl fumarate leading to a ruthenium complex similar to 22: van Wijnkoop, M.; de Lange, P. P. M.; Frühauf, H.-W.; Vieze, K.; Smeets, W. J. J.; Spek, A. L. Organometallics 1995, 14, 4781.
24. 3 in the coupling reaction with olefins: de Lange, P. P. M.; de Boer, R. P.; van Wijnkoop, M.; Ernsting, J. M.; Frühauf, H.-W.; Vieze, K.; Smeets, W. J. J.; Spek, A. L.; Goubitz, K. Organometallics 1993, 12, 440.