Rh(I)-catalyzed cyclization of 1-arylprop-2-yn-1-ol derivatives utilizing rhodium 1,4-migration

Journal of the American Chemical Society

Volumn 127, Issue 10, 2005, Pages 3248-3249

  Yamabe, Hokuto ^a   Mizuno, Akio ^a   Kusama, Hiroyuki ^a   Iwasawa, Nobuharu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 ARYLPROP 2 YN 1 OL; ALCOHOL DERIVATIVE; CYCLOPENTANONE DERIVATIVE; DEUTERIUM; PROPARGYL ALCOHOL; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; HYDROGEN BOND;

EID: 14944374454     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042581o     Document Type: Article

References (28)

1. Wessig, P.; Giombitza, C.; Müller, G.; Teubner, J. J. Org. Chem. 2004, 69, 7582 and references therein.
2. For recent examples of intramolecular Friedel-Crafts-type acylation of 3-phenylpropionic acid derivatives, see: (a) Cui, D.-M.; Zhang, C.; Kawamura, M.; Shimada, S. Tetrahedron Lett. 2004, 45, 1741. (b) Fillion, E.; Fishlock, D. Org. Lett. 2003, 5, 4653. (c) El-Sayrafi, S.; Rayyan, S. Molecules 2001, 6, 279.
3. For recent examples of intramolecular Friedel-Crafts-type acylation of 3-phenylpropionic acid derivatives, see: (a) Cui, D.-M.; Zhang, C.; Kawamura, M.; Shimada, S. Tetrahedron Lett. 2004, 45, 1741. (b) Fillion, E.; Fishlock, D. Org. Lett. 2003, 5, 4653. (c) El-Sayrafi, S.; Rayyan, S. Molecules 2001, 6, 279.
4. For recent examples of intramolecular Friedel-Crafts-type acylation of 3-phenylpropionic acid derivatives, see: (a) Cui, D.-M.; Zhang, C.; Kawamura, M.; Shimada, S. Tetrahedron Lett. 2004, 45, 1741. (b) Fillion, E.; Fishlock, D. Org. Lett. 2003, 5, 4653. (c) El-Sayrafi, S.; Rayyan, S. Molecules 2001, 6, 279.
5. For recent examples of Nazarov-type reactions forming indanone derivatives, see: (a) Kerr, D. J.; Metje, C.; Flynn, B. L. Chem. Commun. 2003, 1380. (b) Clive, D. L. J.; Sannigrahi, M.; Hisaindee, S. J. Org. Chem. 2001, 66, 954. (c) Ready, T. E.; Chien, J. C. W.; Rausch, M. D. J. Organomet. Chem. 1999, 583, 11. (d) Suzuki, T.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1997, 119, 6774.
6. For recent examples of Nazarov-type reactions forming indanone derivatives, see: (a) Kerr, D. J.; Metje, C.; Flynn, B. L. Chem. Commun. 2003, 1380. (b) Clive, D. L. J.; Sannigrahi, M.; Hisaindee, S. J. Org. Chem. 2001, 66, 954. (c) Ready, T. E.; Chien, J. C. W.; Rausch, M. D. J. Organomet. Chem. 1999, 583, 11. (d) Suzuki, T.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1997, 119, 6774.
7. For recent examples of Nazarov-type reactions forming indanone derivatives, see: (a) Kerr, D. J.; Metje, C.; Flynn, B. L. Chem. Commun. 2003, 1380. (b) Clive, D. L. J.; Sannigrahi, M.; Hisaindee, S. J. Org. Chem. 2001, 66, 954. (c) Ready, T. E.; Chien, J. C. W.; Rausch, M. D. J. Organomet. Chem. 1999, 583, 11. (d) Suzuki, T.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1997, 119, 6774.
8. For recent examples of Nazarov-type reactions forming indanone derivatives, see: (a) Kerr, D. J.; Metje, C.; Flynn, B. L. Chem. Commun. 2003, 1380. (b) Clive, D. L. J.; Sannigrahi, M.; Hisaindee, S. J. Org. Chem. 2001, 66, 954. (c) Ready, T. E.; Chien, J. C. W.; Rausch, M. D. J. Organomet. Chem. 1999, 583, 11. (d) Suzuki, T.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1997, 119, 6774.
9. For examples of transition-metal-catalyzed indanone derivatives formation, see: (a) Sanger, A. R. J. Mol. Catal. A: Chem. 2002, 188, 11. (b) Takeuchi, R.; Yasue, H. J. Org. Chem. 1993, 58, 5386. (c) Joh, T.; Doyama, K.; Fujiwara, K.; Maeshima, K.; Takahashi, S. Organometallics 1991, 10, 508. (d) Doyama, K.; Fujiwara, K.; Joh, T.; Maeshima, K.; Takahashi, S. Chem. Lett. 1988, 901.
10. For examples of transition-metal-catalyzed indanone derivatives formation, see: (a) Sanger, A. R. J. Mol. Catal. A: Chem. 2002, 188, 11. (b) Takeuchi, R.; Yasue, H. J. Org. Chem. 1993, 58, 5386. (c) Joh, T.; Doyama, K.; Fujiwara, K.; Maeshima, K.; Takahashi, S. Organometallics 1991, 10, 508. (d) Doyama, K.; Fujiwara, K.; Joh, T.; Maeshima, K.; Takahashi, S. Chem. Lett. 1988, 901.
11. For examples of transition-metal-catalyzed indanone derivatives formation, see: (a) Sanger, A. R. J. Mol. Catal. A: Chem. 2002, 188, 11. (b) Takeuchi, R.; Yasue, H. J. Org. Chem. 1993, 58, 5386. (c) Joh, T.; Doyama, K.; Fujiwara, K.; Maeshima, K.; Takahashi, S. Organometallics 1991, 10, 508. (d) Doyama, K.; Fujiwara, K.; Joh, T.; Maeshima, K.; Takahashi, S. Chem. Lett. 1988, 901.
12. For examples of transition-metal-catalyzed indanone derivatives formation, see: (a) Sanger, A. R. J. Mol. Catal. A: Chem. 2002, 188, 11. (b) Takeuchi, R.; Yasue, H. J. Org. Chem. 1993, 58, 5386. (c) Joh, T.; Doyama, K.; Fujiwara, K.; Maeshima, K.; Takahashi, S. Organometallics 1991, 10, 508. (d) Doyama, K.; Fujiwara, K.; Joh, T.; Maeshima, K.; Takahashi, S. Chem. Lett. 1988, 901.
13. For examples of Friedel-Crafts-type acylation onto heteroaromatic compounds, see: Komoto, I.; Matsuo, J.; Kobayashi, S. Top. Catal. 2002, 19, 43 and references therein.
14. For examples of hydrorhodation, see: (a) Sato, S.; Matsuda, I.; Shibata, M. J. Organomet. Chem. 1989, 377, 347. (b) Sato, S.; Matsuda, I.; Izumi, Y. J. Organomet. Chem. 1989, 359, 255. (c) Sato, S.; Matsuda, L.; Izumi, Y. J. Organomet. Chem. 1988, 344, 71.
15. For examples of hydrorhodation, see: (a) Sato, S.; Matsuda, I.; Shibata, M. J. Organomet. Chem. 1989, 377, 347. (b) Sato, S.; Matsuda, I.; Izumi, Y. J. Organomet. Chem. 1989, 359, 255. (c) Sato, S.; Matsuda, L.; Izumi, Y. J. Organomet. Chem. 1988, 344, 71.
16. For examples of hydrorhodation, see: (a) Sato, S.; Matsuda, I.; Shibata, M. J. Organomet. Chem. 1989, 377, 347. (b) Sato, S.; Matsuda, I.; Izumi, Y. J. Organomet. Chem. 1989, 359, 255. (c) Sato, S.; Matsuda, L.; Izumi, Y. J. Organomet. Chem. 1988, 344, 71.
17. For a review of 1,4-Pd migration, see: (a) Dyker, G. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley: Weinheim, Germany, 1998; p 241. For recent examples of synthetic use of 1,4-Pd migrations, see: (b) Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2002, 124, 14326. (c) Campo, M. A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 11506. (d) Huang, Q.; Campo, M. A.; Yao, T.; Tian, Q.; Larock, R. C. J. Org. Chem. 2004, 69, 8251. The corresponding 1,4-Rh migration has scarcely been utilized. See: (e) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (f) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (e) Miura, T.; Sasaki, T.; Nakazawa, H.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1390.
18. For a review of 1,4-Pd migration, see: (a) Dyker, G. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley: Weinheim, Germany, 1998; p 241. For recent examples of synthetic use of 1,4-Pd migrations, see: (b) Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2002, 124, 14326. (c) Campo, M. A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 11506. (d) Huang, Q.; Campo, M. A.; Yao, T.; Tian, Q.; Larock, R. C. J. Org. Chem. 2004, 69, 8251. The corresponding 1,4-Rh migration has scarcely been utilized. See: (e) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (f) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (e) Miura, T.; Sasaki, T.; Nakazawa, H.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1390.
19. For a review of 1,4-Pd migration, see: (a) Dyker, G. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley: Weinheim, Germany, 1998; p 241. For recent examples of synthetic use of 1,4-Pd migrations, see: (b) Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2002, 124, 14326. (c) Campo, M. A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 11506. (d) Huang, Q.; Campo, M. A.; Yao, T.; Tian, Q.; Larock, R. C. J. Org. Chem. 2004, 69, 8251. The corresponding 1,4-Rh migration has scarcely been utilized. See: (e) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (f) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (e) Miura, T.; Sasaki, T.; Nakazawa, H.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1390.
20. For a review of 1,4-Pd migration, see: (a) Dyker, G. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley: Weinheim, Germany, 1998; p 241. For recent examples of synthetic use of 1,4-Pd migrations, see: (b) Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2002, 124, 14326. (c) Campo, M. A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 11506. (d) Huang, Q.; Campo, M. A.; Yao, T.; Tian, Q.; Larock, R. C. J. Org. Chem. 2004, 69, 8251. The corresponding 1,4-Rh migration has scarcely been utilized. See: (e) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (f) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (e) Miura, T.; Sasaki, T.; Nakazawa, H.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1390.
21. For a review of 1,4-Pd migration, see: (a) Dyker, G. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley: Weinheim, Germany, 1998; p 241. For recent examples of synthetic use of 1,4-Pd migrations, see: (b) Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2002, 124, 14326. (c) Campo, M. A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 11506. (d) Huang, Q.; Campo, M. A.; Yao, T.; Tian, Q.; Larock, R. C. J. Org. Chem. 2004, 69, 8251. The corresponding 1,4-Rh migration has scarcely been utilized. See: (e) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (f) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (e) Miura, T.; Sasaki, T.; Nakazawa, H.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1390.
22. For a review of 1,4-Pd migration, see: (a) Dyker, G. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley: Weinheim, Germany, 1998; p 241. For recent examples of synthetic use of 1,4-Pd migrations, see: (b) Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2002, 124, 14326. (c) Campo, M. A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 11506. (d) Huang, Q.; Campo, M. A.; Yao, T.; Tian, Q.; Larock, R. C. J. Org. Chem. 2004, 69, 8251. The corresponding 1,4-Rh migration has scarcely been utilized. See: (e) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (f) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (e) Miura, T.; Sasaki, T.; Nakazawa, H.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1390.
23. For a review of 1,4-Pd migration, see: (a) Dyker, G. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley: Weinheim, Germany, 1998; p 241. For recent examples of synthetic use of 1,4-Pd migrations, see: (b) Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2002, 124, 14326. (c) Campo, M. A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 11506. (d) Huang, Q.; Campo, M. A.; Yao, T.; Tian, Q.; Larock, R. C. J. Org. Chem. 2004, 69, 8251. The corresponding 1,4-Rh migration has scarcely been utilized. See: (e) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (f) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (e) Miura, T.; Sasaki, T.; Nakazawa, H.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1390.
24. For a review of Rh(I)-catalyzed reactions involving 1,4-addition of aryl rhodium species, see: (a) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169. See also: (b) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
25. For a review of Rh(I)-catalyzed reactions involving 1,4-addition of aryl rhodium species, see: (a) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169. See also: (b) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
26. 3, oxidation of alcoholic substrate 1 was observed.
27. The TMS group of the cyclized products 2i-2k were readily desilylated under the reaction conditions.
28. When TMP was employed as a base, a substantial amount of proton was incorporated to the α-position of the carbonyl. We believe that the proton comes from N-H of TMP via enolization under basic conditions.