Yıl: 2018 Cilt: 42 Sayı: 5 Sayfa Aralığı: 1384 - 1397 Metin Dili: İngilizce DOI: 10.3906/kim-1805-65 İndeks Tarihi: 30-11-2020

Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls

Öz:
Catalytic reactions of α, β -conjugated carbonyl compounds have been a practical tool towards the synthesisof different useful heterocyclic compounds. Despite the numerous reactions with carbon-carbon double bond conjugatedcarbonyls, reactions of acetylenic carbonyls are limited. In this study, efficient dioxole synthesis was carried outvia acetylenic aldehydes and butadiene formation was preferred over cyclopropene formation via acetylenic esters asdifferent functional groups on these substrates change the product distribution. Both reaction conditions (such assolvent and temperature) and electrophilic structure of metal carbenoids alter the product distribution; acceptor (A),donor-acceptor (DA), and acceptor-acceptor (AA) functionalized diazo compounds yield different product types overdifferent mechanisms.
Anahtar Kelime:

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • 1. Corey, E. J.; Cheng, X. M. The Logic of Chemical Synthesis; Wiley: New York, NY, USA, 1989.
  • 2. Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis; Wiley VCH: Weinheim, Germany, 1996.
  • 3. Denizaltı, S.; Telli F. Ç.; Yıldıran, S.; Salman, A. Y.; Çetinkaya, B. Turk. J. Chem. 2016, 40, 689-697.
  • 4. Li, A. H.; Dai, L. X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341-2371.
  • 5. Dai, L. X.; Hou, X. L.; Zhou, Y. G. Pure Appl. Chem. 1999, 71, 369-376.
  • 6. Gaunt, M. J.; Johansson, C. C. C. Chem. Rev. 2007, 107, 5596-5605.
  • 7. Son, S.; Fu, G. C. J. Am. Chem. Soc. 2007, 129, 1046-1047.
  • 8. Shiina, I.; Ibuka, R. Tetrahedron Lett. 2001, 42, 6303-6305.
  • 9. Wang, Z.; Wen, J.; Bi, Q. W.; Xu, X. Q.; Shen, Z. Q.; Li, X. X.; Chen, Z. Tetrahedron Lett. 2014, 55, 2969-2972.
  • 10. DeAngelis, A.; Panne, P.; Yap, G. P. A.; Fox, J. M. J. Org. Chem. 2008, 73, 1435-1430.
  • 11. Manna, S.; Antonchick, A. P. Angew. Chem. Int. Ed. 2015, 127, 15058-15061.
  • 12. Aggarwal, V. K.; Alonso, E.; Fang, G. Y.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433-1436.
  • 13. Lebel, H.; Marcoux, J. F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977-1050.
  • 14. Liao, W. W.; Li, K.; Tang, Y. J. Am. Chem. Soc. 2003, 125, 13030-13031.
  • 15. Papageorgiou, C. D.; Cubillo de Dios, M. A.; Ley, S. V.; Gaunt, M. J. Angew. Chem. Int. Ed. 2004, 43, 4641-4644.
  • 16. Aggarwal, V. K.; Grange, E. Chem. Eur. J. 2006, 12, 568-575.
  • 17. Charette, A. B.; Janes, M. K.; Lebel, H. Tetrahedron Asymmetry 2003, 14, 867-872.
  • 18. Russell, A. E.; Brekan, J.; Groenberg, L.; Doyle, M. P. J. Org. Chem. 2004, 69, 5269-5274.
  • 19. Phun, L. H.; Aponte-Guzman, J.; France, S. Angew. Chem. Int. Ed. 2012, 51, 3198-3202.
  • 20. McGarrigle, E. M.; Myers, E. L.; Illa, O.; Shaw, M. A.; Riches, S. L.; Aggarwal, V. K. Chem. Rev. 2007, 107, 5841-5883.
  • 21. Huisgen, R.; March, P. J. Am. Chem. Soc. 1982, 104, 4953-4954.
  • 22. Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F.; Spiga, M. Org. Lett. 2005, 7, 4565-4568.
  • 23. Davies, H. M. L.; Ahmed, G.; Calvo, R. L.; Churchill, M. R.; Churchill, D. G. J. Org. Chem. 1998, 63, 2641-2645.
  • 24. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263-309.
  • 25. Storm, D. L.; Spencer, T. A. Tetrahedron Lett. 1967, 8, 1865-1867.
  • 26. Spencer, T. A.; Villarica, R. M.; Storm, D. L.; Weaver, T. D.; Friary, R. J.; Posler, J.; Shafer, P. R. J. Am. Chem. Soc. 1967, 89, 5497-5499.
  • 27. Murayama, S. T.; Spencer, T. A. Tetrahedron Lett. 1969, 10, 4479-4482.
  • 28. Anac, O.; Sezer, O.; Candan, O.; Güngor, F. S.; Cansever, M. S. Tetrahedron Lett. 2008, 49, 1062-1065.
  • 29. Merey, G.; Kaya, M.; Anaç, O. Helv. Chim. Acta 2012, 95, 1409-1424.
  • 30. Anac, O.; Daut, A. Liebigs Ann.-Recl. 1997, 1249-1254.
  • 31. Anaç, O.; Gungor, F. S.; Merey, G. Helv. Chim. Acta 2006, 89, 1231-1240.
  • 32. Yurtsever, M.; Celik, M. A.; Tuzun, N. S.; Gungor, F. S.; Sezer, O.; Anaç, O. Organometallics 2007, 26, 2978-2985.
  • 33. England, D. B.; Eagan, J. M.; Merey, G.; Anac, O.; Padwa, A. Tetrahedron 2008, 64, 988-1001.
  • 34. Anaç, O.; Gungor, F. S. Tetrahedron 2010, 66, 5931-5953.
  • 35. Merey, G.; Anac, O. Helv. Chim. Acta 2011, 94, 1053-1064.
  • 36. Anac, O.; Gungor, F. S.; Sezer, O. Helv. Chim. Acta 2011, 94, 1115-1129.
  • 37. Zhou, J. L.; Wang, L. J.; Xu, H.; Sun, X. L.; Tang, Y. ACS Catal. 2013, 3, 685-688.
  • 38. Liu, C. R.; Zhu, B. H.; Zheng, J. C.; Sun, X. L.; Xie, Z. W.; Tang, Y. Chem. Commun. 2011, 47, 1342-1344.
  • 39. Zhou, J. L.; Liang, Y.; Deng, C.; Zhou, H.; Wang, Z.; Sun, X. L.; Zheng, J. C.; Yu, Z. X.; Tang, Y. Angew. Chem. Int. Ed. 2011, 50, 7874-7878.
  • 40. Hamaguchi, M.; Matsubara, H.; Nagai, T. J. Org. Chem. 2001, 66, 5395-5404.
  • 41. Pavlyuk, O.; Telle, H.; McMills, M. C. Tetrahedron Lett. 2009, 50, 2716-2718.
  • 42. Paulissen, R.; Hayez, E.; Hubert, A. J.; Teyssie, P. Tetrahedron Lett. 1974, 15, 607-608.
  • 43. Kantorowski, E. J.; Kurth, M. J. Mol. Divers. 1996, 2, 207-216.
  • 44. Whitehouse, D. L.; Nelson, K. H. Jr.; Savinov, S. N.; Lowe, R. S.; Austin, D. J. Bioorg. Med. Chem. 1998, 6, 1273-1282.
  • 45. Ibata, T.; Hamaguchi, M.; Kiyohara, H. Chem. Lett. 1975, 4, 21-24.
  • 46. Deng, G.; Wang, F.; Lu, S.; Cheng, B. Org. Let. 2015, 17, 4651-4653.
  • 47. Dermenci, A.; Whittaker, R. E.; Gao, Y.; Cruz, F. A.; Yu, Z. X.; Dong, G. Chem. Sci. 2015, 6, 3201-3210.
  • 48. Whittaker, R. E.; Dong, G. Org. Lett. 2015, 17, 5504-5507.
  • 49. Vasin, V. A.; Bezrukova, E. V.; Razin, V. V.; Somov, N. V. Russ. J. Org. Chem. 2017, 53, 1763-1765.
  • 50. Zhao, L. B.; Guan, Z. H.; Han, Y.; Xie, Y. X.; He, S.; Liang, Y. M. J. Org. Chem. 2007, 72, 10276-10278.
  • 51. Gong, J.; Zhao, Z.; Zhang, F.; Wu, S.; Yan, G.; Quan, Y.; Ma, B. Org. Lett. 2014, 16, 5524-5527.
  • 52. Magar, K. B. S.; Lee, Y. R.; Kim, S. H. Mol. Divers. 2013, 17, 679-691.
  • 53. Schinnerl, M.; Bohm, C.; Seitz, M.; Reiser, O. Tetrahedron Asymmetry 2003, 14, 765-771.
  • 54. Guerrero-Vasquez, G. A.; Galarza, F. A. D.; Molinillo, J. M. G.; Andrade, C. K. Z.; Macias, F. A. Eur. J. Org. Chem. 2016, 2016, 1599-1605.
  • 55. Kadirvel, M.; Fanimarvasti, F.; Forbes, S.; McBain, A.; Gardiner, J. M.; Brown, G. D.; Freeman, S. Chem. Commun. 2014, 50, 5000-5002.
  • 56. Yamamoto, N.; Iida, T.; Saito, N. Patent JP 1995-230474, 1995.
  • 57. Kamatani, T.; Yukawa, H.; Honda, T. J. Chem. Soc., Chem. Commun. 1986, 0, 651.
APA Güngör F, Ozguz E, Anac O, Tarakçı N, Merey G (2018). Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls. , 1384 - 1397. 10.3906/kim-1805-65
Chicago Güngör Füsun Seyma,Ozguz Emre,Anac Olcay,Tarakçı Nurdan,Merey Gokce Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls. (2018): 1384 - 1397. 10.3906/kim-1805-65
MLA Güngör Füsun Seyma,Ozguz Emre,Anac Olcay,Tarakçı Nurdan,Merey Gokce Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls. , 2018, ss.1384 - 1397. 10.3906/kim-1805-65
AMA Güngör F,Ozguz E,Anac O,Tarakçı N,Merey G Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls. . 2018; 1384 - 1397. 10.3906/kim-1805-65
Vancouver Güngör F,Ozguz E,Anac O,Tarakçı N,Merey G Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls. . 2018; 1384 - 1397. 10.3906/kim-1805-65
IEEE Güngör F,Ozguz E,Anac O,Tarakçı N,Merey G "Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls." , ss.1384 - 1397, 2018. 10.3906/kim-1805-65
ISNAD Güngör, Füsun Seyma vd. "Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls". (2018), 1384-1397. https://doi.org/10.3906/kim-1805-65
APA Güngör F, Ozguz E, Anac O, Tarakçı N, Merey G (2018). Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls. Turkish Journal of Chemistry, 42(5), 1384 - 1397. 10.3906/kim-1805-65
Chicago Güngör Füsun Seyma,Ozguz Emre,Anac Olcay,Tarakçı Nurdan,Merey Gokce Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls. Turkish Journal of Chemistry 42, no.5 (2018): 1384 - 1397. 10.3906/kim-1805-65
MLA Güngör Füsun Seyma,Ozguz Emre,Anac Olcay,Tarakçı Nurdan,Merey Gokce Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls. Turkish Journal of Chemistry, vol.42, no.5, 2018, ss.1384 - 1397. 10.3906/kim-1805-65
AMA Güngör F,Ozguz E,Anac O,Tarakçı N,Merey G Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls. Turkish Journal of Chemistry. 2018; 42(5): 1384 - 1397. 10.3906/kim-1805-65
Vancouver Güngör F,Ozguz E,Anac O,Tarakçı N,Merey G Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls. Turkish Journal of Chemistry. 2018; 42(5): 1384 - 1397. 10.3906/kim-1805-65
IEEE Güngör F,Ozguz E,Anac O,Tarakçı N,Merey G "Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls." Turkish Journal of Chemistry, 42, ss.1384 - 1397, 2018. 10.3906/kim-1805-65
ISNAD Güngör, Füsun Seyma vd. "Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls". Turkish Journal of Chemistry 42/5 (2018), 1384-1397. https://doi.org/10.3906/kim-1805-65