Synthesis of 3,5-disubstituted cyclohex-2-en-1-one via a five-step domino reaction catalyzed by secondary amines: Formation of (e)-α,β-unsaturated methyl ketones

Asian Journal of Organic Chemistry

Volumn 2, Issue 12, 2013, Pages 1026-1030

  Ghorai, Manas K ^a   Samanta, Sauvik ^a   Das, Subhomoy ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

Aldehydes; Aldol reaction; Amine catalysis; Domino reaction; Michael addition

Indexed keywords

EID: 84899860834     PISSN: 21935807     EISSN: 21935807     Source Type: Journal    
DOI: 10.1002/ajoc.201300142     Document Type: Article

References (63)

1. M. A. González, S. Ghosh, F. Rivas, D. Fischer, E. A. Theodorakis, Tetrahedron Lett. 2004, 45, 5039-5041;
2. C. S. Letizia, J. Cocchiara, G. A. Wellington, C. Funk, A. M. Api, Food Chem. Toxicol. 2000, 38, S153-S155;
3. B. H. Bae, K. S. Im, W. C. Choi, J. Hong, C. O. J. Lee, S. Choi, B. W. Son, J. I. Song, J. H. Jung, J. Nat. Prod. 2000, 63, 1511-1514;
4. H. Yamamoto, J. H. Sham, J. Am. Chem. Soc. 1979, 101, 1609-1611;
5. K. N. Campbell, A. Schrage, B. K. Campbell, J. Org. Chem. 1950, 15, 1139-1141;
6. P. J. Mohr, R. L. Halcomb, J. Am. Chem. Soc. 2003, 125, 1712-1713;
7. A. Goeke, D. Mertl, G. Brunner, Angew. Chem. 2005, 117, 101-103;
8. A. Goeke, D. Mertl, G. Brunner, Angew. Chem. Int. Ed. 2005, 44, 99-101;
9. R. Lakshmi, T. D. Bateman, M. C. McIntosh, J. Org. Chem. 2005, 70, 5313-5315;
10. G. P-J. Hareau, M. Koiwa, S. Hikichi, F. Sato, J. Am. Chem. Soc. 1999, 121, 3640-3650;
11. S. Yamashita, K. Iso, M. Hirama, Org. Lett. 2008, 10, 3413-3415.
12. K. Mori, T. Katoh, T. Suzuki, T. Noji, M. Yamanaka, T. Akiyama, Angew. Chem. 2009, 121, 9832-9834;
13. K. Mori, T. Katoh, T. Suzuki, T. Noji, M. Yamanaka, T. Akiyama, Angew. Chem. Int. Ed. 2009, 48, 9652-9654;
14. N. Itagaki, T. Sugahara, Y. Iwabuchi, Org. Lett. 2005, 7, 4181-4183;
15. C. Pidathala, L. Hoang, N. Vingola, B. List, Angew. Chem. 2003, 115, 2891-2894;
16. C. Pidathala, L. Hoang, N. Vingola, B. List, Angew. Chem. Int. Ed. 2003, 42, 2785-2788.
17. C. Agami, H. Sevestre, J. Chem. Soc. Chem. Commun. 1984, 1385-1386;
18. C. Agami, N. Platzer, H. Sevestre, Bull. Soc. Chim. Fr. 1987, 2, 358-360.
19. Z. G. Hajos, D. R. Parrish, Germany Patent DE 21022623, 1971;
20. Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621;
21. U. Eder, G. R. Sauer, R. Wiechert, Germany Patent DE 2014757, 1971;
22. U. Eder, G. R. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492-493;
23. U. Eder, G. R. Sauer, R. Wiechert, Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497;
24. Z. G. Hajos, D. R. Parrish, Org. Synth. 1990, 7, 363;
25. Z. G. Hajos, D. R. Parrish, Org. Synth. 1985, 63, 26;
26. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471-5569.
27. P. Wieland, K. Miescher, Helv. Chim. Acta 1950, 33, 2215-2228.
28. J. Zhou, V. Wakchaure, P. Kraft, B. List, Angew. Chem. 2008, 120, 7768-7771;
29. J. Zhou, V. Wakchaure, P. Kraft, B. List, Angew. Chem. Int. Ed. 2008, 47, 7656-7658;
30. L. Chen, S. Luo, J. Li, X. Li, J. P. Cheng, Org. Biomol. Chem. 2010, 8, 2627-2632.
31. S. Qi, K. Shi, H. Gao, Q. Liu, H. Wang, Molecules 2007, 12, 988-996;
32. D. Jyothi, S. H. Prasad, Indian J. Chem. 2008, 47B, 630-632;
33. Y. Q. Yang, Z. Chai, H. F. Wang, X. K. Chen, H. H. Cui, C. W. Zheng, H. Xiao, P. Li, G. Zhao, Chem. Eur. J. 2009, 15, 13295-13298;
34. G. Majetich, S. Allen, Arkivoc 2010, iv, 104-124;
35. S. Biswas, S. Maiti, U. Jana, Eur. J. Org. Chem. 2010, 2861-2866;
36. Y. Izawa, D. Pun, S. S. Stahl, Science 2011, 333, 209-213.
37. H. Naka, Y. Kaneda, T. Kurata, J. Oleo Sci. 2001, 50, 813-821;
38. T. Ishikawa, R. Kadoya, M. Arai, H. Takahasi, Y. Kaisi, T. Mizuta, K. Yoshikai, S. Saito, J. Org. Chem. 2001, 66, 8000-8009;
39. L. Tuchman-Shukron, T. Kehat, M. Portnoy, Eur. J. Org. Chem. 2009, 992-996;
40. G. Kehat, K. Goren, M. Portnoy, New J. Chem. 2012, 36, 394-401.
41. M. K. Ghorai, A. Kumar, S. Halder, Tetrahedron 2007, 63, 4779-4787;
42. M. K. Ghorai, K. Ghosh, A. K. Yadav, Tetrahedron Lett. 2009, 50, 476-479;
43. M. K. Ghorai, S. Halder, R. K. Das, J. Org. Chem. 2010, 75, 7061-7072;
44. M. K. Ghorai, S. Halder, S. Samanta, Aust. J. Chem. 2012, 65, 1262-1270;
45. M. K. Ghorai, K. Ghosh, A. K. Yadav, Y. Nanaji, S. Halder, M. Sayyad, J. Org. Chem. 2013, 78, 2311-2326.
46. D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811-891;
47. M. E. Jung, in: Comprehensive Organic Synthesis, Vol.4 (Eds.: B.M. Trost, I. Fleming, C.H. Heathcock), Pergamon Elsevier, Oxford, 1991, pp.1-67;
48. V. J. Lee in Comprehensive Organic Synthesis, Vol.4 (Eds.: B.M. Trost, I. Fleming, C.H. Heathcock), Pergamon Elsevier, Oxford, 1991, pp.69-168;
49. J. A. Kozlowski in Comprehensive Organic Synthesis, Vol.4, (Eds.: B.M. Trost, I. Fleming, C.H. Heathcock), Pergamon Elsevier, Oxford, 1991, pp.169-198;
50. P. Perlmutter in Conjugate Addition Reactions in Organic Synthesis Pergamon Elsevier, Oxford, 1992, pp.63-197.
51. K. Zumbansen, A. Döhring, B. List, Adv. Synth. Catal. 2010, 352, 1135-1138;
52. M. Bellassoued, J. Aatar, M. Bouzid, M. Damak, Phosphorus Sulfur Silicon 2010, 185, 1886-1895;
53. Y. Chi, S. T. Scroggins, E. Boz, J. M. J. Fréchet, J. Am. Chem. Soc. 2008, 130, 17287-17289;
54. S. Abelló, D. Vijaya-Shankar, J. Pérez-Ramírez, Appl. Catal. A 2008, 342, 119-125;
55. S.-D. Yang, L.-Y. Wu, Z.-L. Yan, Z.-L. Pan, Y.-M. Liang, J. Mol. Catal. A 2007, 268, 107-111;
56. A. Kumar, Akhanska, J. Mol. Catal. A 2007, 274, 212-216.
57. F. Orsini, F. Pelizzoni, M. Rorte, R. Destro, P. Gariboldi, Tetrahedron 1988, 44, 519-541;
58. T. Kano, J. Takai, O. Tokuda, K. Maruoka, Angew. Chem. 2005, 117, 3115-3117;
59. T. Kano, J. Takai, O. Tokuda, K. Maruoka, Angew. Chem. Int. Ed. 2005, 44, 3055-3057;
60. C. Isart, J. Burés, J. Vilarrasa, Tetrahedron Lett. 2008, 49, 5414-5418;
61. X. Companyó, G. Valero, A. Moyano, R. Rios, Chem. Eur. J. 2009, 15, 6564-6568.
62. T. Mandal, C. G. Zhao, Tetrahedron Lett. 2007, 48, 5803-5806;
63. S. Samanta, J. Krause, T. Mandal, C. G. Zhao, Org. Lett. 2007, 9, 2745-2748.