New and facile approach for the synthesis of (E)-α,β-unsaturated esters and ketones

Chemistry - A European Journal

Volumn 16, Issue 39, 2010, Pages 11840-11842

  China Raju, Bhimapaka ^a   Suman, Pathi ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

esters; ketones; piperidine; stereoselectivity; synthetic methods

Indexed keywords

CARBONYL COMPOUNDS; DIKETONES; PIPERIDINE; SYNTHETIC METHODS; UNSATURATED ESTERS;

CARBONYLATION; DICHLOROMETHANE; ESTERIFICATION; KETONES; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL); UNSATURATED COMPOUNDS;

ESTERS;

EID: 78249259341     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000883     Document Type: Article

References (48)

1. B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863 - 927
2. K. S. Petersen, G. H. Posner, Org. Lett. 2008, 10, 4685 - 4687
3. D. K. Barma, A. Kundu, A. Bandyopadhayay, A. Kundu, B. Sangras, A. Briot, C. Mioskowski, J. R. Falck, Tetrahedron Lett. 2004, 45, 5917 - 5920
4. J. M. Concellón, H. Rodriguez-Solla, C. Mejica, Tetrahedron 2006, 62, 3292 - 3300
5. H. M. Sampath Kumar, M. Shesha Rao, S. Joyasawal, J. S. Yadav, Tetrahedron Lett. 2003, 44, 4287 - 4289
6. M. Yu, G. Li, S. Wang, L. Zhang, Adv. Synth. Catal. 2007, 349, 871 - 875
7. J. S. Yadav, B. V. S. Reddy, M. K. Gupta, U. Dash, S. K. Pandey, Synlett 2007, 0809 - 0811.
8. M. W. Smith, R. Hunter, D. J. Patten, W. Hinz, Tetrahedron Lett. 2009, 50, 6342 - 6346
9. O. Corminboeuf, L. E. Overman, L. D. Pennington, J. Org. Chem. 2009, 74, 5458 - 5470
10. A. Nakhai, J. Bergman, Tetrahedron 2009, 65, 2298 - 2306
11. T. Miyake, H. Kigoshi, H. Akita, Tetrahedron: Asymmetry 2007, 18, 2915 - 2922.
12. C. J. O'Brien, J. L. Tellez, Z. S. Nixon, L. J. Kang, A. L. Carter, S. R. Kunkel, K. C. Przeworski, G. A. Chass, Angew. Chem. 2009, 121, 6968 - 6971
13. Angew. Chem. Int. Ed. 2009, 48, 6836 - 6839
14. J. McNulty, P. Das, Eur. J. Org. Chem. 2009, 4031 - 4035
15. N. A. Piro, C. C. Cummins, J. Am. Chem. Soc. 2009, 131, 8764 - 8765
16. B. List, A. Doehring, T. H. Fonseca, K. Wobser, H. Thienen, R. R. Torres, P. L. Galilea, Adv. Synth. Catal. 2005, 347, 1558 - 1560
17. B. M. Choudary, K. Mahendar, M. L. Kantam, K. V. S. Ranganath, T. Athar, Adv. Synth. Catal. 2006, 348, 1977 - 1985
18. Z. Z. Huang, S. Ye, W. Xia, Y.-H. Yu, Y. Tang, J. Org. Chem. 2002, 67, 3096 - 3103.
19. B. List, A. Doehring, M. T. H. Fonseca, A. Job, R. R. Torres, Tetrahedron 2006, 62, 476 - 482.
20. A. Galat, J. Am. Chem. Soc. 1945, 67, 376 - 377
21. C. J. Martin, A. I. Schepartz, B. F. Daubert, J. Am. Chem. Soc. 1948, 70, 2601 - 2602
22. J. Klein, E. D. Bergmann, J. Am. Chem. Soc. 1957, 79, 3452 - 3454
23. J. Shabtai, E. Ney-Igner, H. Pines, J. Org. Chem. 1981, 46, 3795 - 3802.
24. G. A. Mirafzal, G. Cheng, L. K. Woo, J. Am. Chem. Soc. 2002, 124, 176 - 177
25. Y. Chen, L. Huang, M. A. Ranade, X. P. Zhang, J. Org. Chem. 2003, 68, 3714 - 3717.
26. S. Sebti, A. Solhy, R. Tahir, S. Boulaajaj, J. A. Mayoral, J. M. Fraile, A. Kossir, H. Oumimoun, Tetrahedron Lett. 2001, 42, 7953 - 7955
27. J. S. Yadav, B. V. S. Reddy, P. Vishnumurthy, Tetrahedron Lett. 2008, 49, 4498 - 4500
28. J. Wang, M. Lei, Q. Li, Z. Ge, X. Wang, R. Li, Tetrahedron 2009, 65, 4826 - 4833
29. J. Dheur, M. Sauthier, Y. Casanet, A. Mortreux, Adv. Synth. Catal. 2007, 349, 2499 - 2506.
30. B. C. Ranu, R. Jana, Eur. J. Org. Chem. 2006, 3767 - 3770
31. T. Sugino, K. Tanaka, Chem. Lett. 2001, 110 - 111.
32. M. V. Pryadeina, O. G. Kuzueva, Ya. V. Burgart, V. I. Saloutin, K. A. Lyssenko, M. Yu. Antipin, J. Fluorine Chem. 2002, 117, 1 - 7
33. I. Katsuyama, K. Funabiki, M. Matsui, H. Muramatsu, K. Shibata, Chem. Lett. 1996, 179 - 180.
34. C. Srinivas, C. N. S. Sai Pavan Kumar, B. China Raju, V. Jayathirtha Rao, V. G. M. Naidu, S. Ramakrishna, P. V. Diwan, Bioorg. Med. Chem. Lett. 2009, 19, 5915 - 5918
35. B. China Raju, A. K. Tiwari, J. Ashok Kumar, A. Z. Ali, S. B. Agawane, G. Saidachary, K. Madhusudana, Bioorg. Med. Chem. 2010, 18, 358 - 365
36. B. Gangadasu, B. China Raju, V. Jayathirtha Rao, J. Heterocycl. Chem. 2009, 46, 1213 - 1217
37. P. Narender, M. Ravinder, S. Partha Sarathi, B. China Raju, C. Ramesh, V. Jayathirtha Rao, Helv. Chim. Acta 2009, 92, 959 - 966
38. B. Gangadasu, P. Narender, S. B. Kumar, M. Ravinder, B. Ananda Rao, C. Ramesh, B. China Raju, V. Jayathirtha Rao, Tetrahedron 2006, 62, 8398 - 8403.
39. B. Gangadasu, M. Janaki Ram Reddy, M. Ravinder, S. Bharath Kumar, B. China Raju, K. Pranay Kumar, U. S. N. Murthy, V. Jayathirtha Rao, Eur. J. Med. Chem. 2009, 44, 4661 - 4667.
40. Y. Shen, Yuefen Zhou, Tetrahedron Lett. 1991, 32, 513 - 514
41. G. Elias, M. N. A. Rao, Eur. J. Med. Chem. 1988, 23, 379 - 380
42. T. P. Robinson, R. B. Hubbard, T. J. Ehlers, J. L. Arbiser, D. J. Goldsmith, J. P. Bowena, Bioorg. Med. Chem. 2005, 13, 4007 - 4013
43. T. Thiemann, M. Watanabe, Y. Tanaka, S. Mataka, New J. Chem. 2004, 28, 578 - 584
44. D. S. Brown, B. A. Marpla, P. Smith, L. Walton, Tetrahedron 1995, 51, 3587 - 3606
45. E. Breuer, D. M. Bannet, Tetrahedron 1978, 34, 997 - 1002
46. L. Marc, D. Alain, J. Am. Chem. Soc. 1981, 103, 877 - 878
47. C. Peppe, R. P. Das Chagas, J. Organomet. Chem. 2006, 691, 5856 - 5860
48. B. Abdelmalek, D. Abdelmadjid, R. Salah, C. Bertrand, B. Ali, J. Heterocycl. Chem. 2008, 45, 329 - 333.