Phosphine-mediated reaction of 3-alkyl allenoates and diaryl 1,2-diones: Efficient diastereoselective synthesis of fully substituted cyclopentenones

Organic Letters

Volumn 15, Issue 8, 2013, Pages 1858-1861

  Jose, Anu ^a   Seetha Lakshmi, K C ^a   Suresh, Eringathodi ^b   Nair, Vijay ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84876582810     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400467v     Document Type: Article

References (71)

1. Acheson, R. M. Adv. Heterocycl. Chem. 1963, 1, 125
2. Winterfeidt, E. Angew. Chem., Int. Ed. Engl. 1967, 6, 423
3. Huisgen, R. In Topics in Heterocyclic Chemistry; Castle, R., Ed.; John Wiley and Sons: New York, 1969; Chapter 8, p 223.
4. Nair, V.; Menon, R. S.; Sreekanth, A. R.; Abhilash, N.; Biju, A. T. Acc. Chem. Res. 2006, 39, 520
5. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. Engl. 2000, 39, 3168
6. Dömling, A. Chem. Rev. 2006, 106, 17
7. Scheffelaar, R.; Ruijter, E.; Orru, R. V. A. Multicomponent Reaction Design Strategies: Towards Scaffold and Stereochemical Diversity Top. Heterocycl. Chem. 2010, 25, 95
8. Ramon, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602
9. Zhu, J. Eur. J. Org. Chem. 2003, 1133
10. Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899
11. Nair, V.; Babu, B. P.; Varghese, V.; Sinu, C. R.; Paul, R. R.; Anabha, E. R.; Suresh, E. Tetrahedron Lett. 2009, 50, 3716
12. Nair, V.; Deepthi, A.; Beneesh, P. B.; Suresh, E. Synthesis 2006, 1443
13. Nair, V.; Devipriya, S.; Suresh, E. Tetrahedron 2008, 64, 3567
14. Yavari, I.; Mirzaei, A.; Moradi, L.; Khalili, G. Tetrahedron Lett. 2010, 51, 396
15. Yavari, I.; Mokhtarporyani-Sanandaj, A.; Moradi, L.; Mirzaei, A. Tetrahedron 2008, 64, 5221
16. Ma, C.; Ding, H.; Wang, Y. Org. Lett. 2006, 8, 3133
17. Ma, C.; Yang, Y. W. Org. Lett. 2005, 7, 1343
18. Terzidis, M. A.; Stephanidou-Stephanatou, J.; Tsoleridis, C. A.; Terzis, A.; Raptopoulou, C. P.; Psycharis, V. Tetrahedron 2010, 66, 947
19. Diels, O.; Alder, K. Liebigs Ann. Chem. 1932, 498, 16
20. Huisgen, R.; Morikawa, M.; Herbig, K.; Brunn, E. Chem. Ber. 1967, 100, 1094
21. Johnson, A. W.; Tebby, J. C. J. Chem. Soc. 1961, 2126
22. Tebby, J. C.; Wilson, I. F.; Grifiths, D. V. J. Chem. Soc., Perkin Trans. 1 1979, 2133
23. Acheson, R. M.; Plunkett, A. O. J. Chem. Soc. 1964, 2676
24. Winterfeldt, E. Chem. Ber. 1964, 97, 1952
25. Winterfeldt, E.; Dillinger, H. J. Chem. Ber. 1966, 99, 1558
26. Winterfeldt, E.; Schumann, D.; Dillinger, H. J. Chem. Ber. 1969, 102, 1656
27. Dillinger, H. J.; Fengler, G.; Schumann, D.; Winterfeldt, E. Tetrahedron 1974, 30, 2553 and 2561
28. Junjappa, H.; Saxena, M. K.; Ramaiah, D.; Lohray, B. B.; Rath, N. P.; George, M. V. J. Org. Chem. 1998, 63, 9801
29. Huisgen, R. In The Adventure Playground of Mechanisms and Novel Reactions: Profiles, Pathways and Dreams; Seeman, J. I., Ed.; American Chemical Society: Washington, DC, 1994; p 62.
30. Nair, V.; Biju, A. T.; Mathew, S. C.; Babu, B. P. Chem.-Asian J. 2008, 3, 810
31. Huisgen, R.; Blaschke, H.; Brunn, E. Tetrahedron Lett. 1966, 7, 405
32. Brunn, E.; Huisgen, R. Angew. Chem., Int. Ed. 1969, 8, 513
33. Mitsunobu, O. Synthesis 1981, 1
34. Hughs, D. L. Org. Prep. Proced. Int. 1996, 28, 127
35. Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140
36. Yu, S.; Ma, S. Angew. Chem., Int. Ed. 2012, 51, 2
37. Zhao, Q.-Y.; Lian, Z.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 1724
38. Cowen, B. J.; Miller, S. J. Chem. Soc. Rev. 2009, 38, 3102
39. Ma, S. Chem. Rev. 2005, 105, 2829
40. Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035
41. Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535
42. Xiao, H.; Chai, Z.; Cao, D.; Wang, H.; Chen, J.; Zhao, G. Org. Biomol. Chem. 2012, 10, 3195
43. Chen, X.-Y.; Lin, R.-C.; Ye, S. Chem. Commun. 2012, 48, 1317
44. Chen, X.-Y.; Ye, S. Eur. J. Org. Chem. 2012, 5723
45. Steurer, M.; Jensen, K. L.; Worgull, D.; Jørgensen, K. A. Chem.-Eur. J. 2012, 18, 76
46. Wang, D.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 2764
47. Wang, Y.; Yu, Z.-H.; Zheng, H.-F.; Shi, D.-Q. Org. Biomol. Chem. 2012, 10, 7739
48. Na, R.; Jing, C.; Xu, Q.; Jiang, H.; Wu, X.; Shi, J.; Zhong, J.; Wang, M.; Benitez, D.; Tkatchouk, E.; Goddard, W. A., III; Guo, H.; Kwon, O. J. Am. Chem. Soc. 2011, 133, 13337
49. Wang, T.; Ye, S. Org. Biomol. Chem. 2011, 9, 5260
50. Szeto, J.; Sriramurthy, V.; Kwon, O. Org. Lett. 2011, 13, 5420
51. Fujiwara, Y.; Fu, G. C. J. Am. Chem. Soc. 2011, 133, 12293
52. Nair, V.; Paul, R. R.; Suresh, E. Synthesis 2010, 3741
53. Nair, V.; Vidya, N.; Abhilash, K. G. Org. Biomol. Chem. 2008, 6, 1738
54. Nair, V.; Pillai, A. N.; Suresh, C. H. Chem.-Eur. J. 2008, 14, 5851
55. Nair, V.; Biju, A. T.; Abhilash, K. G.; Menon, R. S.; Suresh, E. Org. Lett. 2005, 7, 2121
56. Nair, V.; Pillai, A. N.; Menon, R. S.; Suresh, E. Org. Lett. 2005, 7, 1189
57. Zhu, X.-F.; Henry, C. E.; Wang, J.; Dudding, T.; Kwon, O. Org. Lett. 2005, 7, 1387
58. Zhu, X.-F.; Schaffner, A.-P.; Li, C. R.; Kwon, O. Org. Lett. 2005, 7, 2977
59. Ma, R.; Xu, S.; Tang, X.; Wu, G.; He, Z. Tetrahedron 2011, 67, 1053
60. Xu, S.; Zhou, L.; Ma, R.; Song, H.; He, Z. Org. Lett. 2010, 12, 544
61. Xu, S.; Zhou, L.; Zeng, S.; Ma, R.; Wang, Z.; He, Z. Org. Lett. 2009, 11, 3498
62. Xu, S.; Zhou, L.; Ma, R.; Song, H.; He, Z. Chem.-Eur. J. 2009, 15, 8698
63. Pace-Asciak, C.; Granström, E. Prostaglandins and Related Substances; Elsevier: New York, 1983.
64. Nicolaou, A.; Kokotos, G. Prostanoids. In Bioactive Lipids; Oily Press: Bridgwater, 2004; p 197.
65. Römpp Lexikon Naturstoffe; Fugmann, B.; Lane-Fugmann, S.; Steglich, W., Eds.; Thieme: Stuttgart, 1997.
66. Bindra, J. S. The Synthesis of Prostaglandins. In Total Synthesis of Natural Products; ApSimon, J., Ed.; John Wiley & Sons, Inc.: Hoboken, 2007; Vol. 4, Chapter 4.
67. Molecular Action of Insecticides on Ion Channels; American Chemical Society: Washington, DC, 1995; ACS Syp. Ser. 591, p 2643.
68. Handbook of Pesticide Toxicology; Hayes, W. J., Ed.; Academic Press: New York, 1991; p 585.
69. Holtz, E.; Köhler, V.; Appel, B.; Langer, P. Eur. J. Org. Chem. 2005, 532
70. Yang, J.-S.; Huang, H.-H.; Lin, S.-H. J. Org. Chem. 2009, 74, 3974
71. Romero, J. M. L.; Sapmaz, S.; Fensterbank, L.; Malacria, M. Eur. J. Org. Chem. 2001, 767