Organocatalyzed enantioselective synthesis of 2-amino-5-oxo-5,6,7,8- tetrahydro-4H-chromene-3-carboxylates

Tetrahedron Letters

Volumn 52, Issue 50, 2011, Pages 6792-6795

  Ramireddy, Naresh ^a   Abbaraju, Santhi ^a   Zhao, Cong Gui ^a  

^a UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

Author keywords

1,3 Cyclohexanedione; 4H Chromene; Cinchona thiourea; Enantioselective; Organocatalysis; Tandem reaction

Indexed keywords

2 AMINO 5 OXO 5,6,7,8 TETRAHYDRO 4H CHROMENE 3 CARBOXYLATE; 5,5 DIMETHYL 1,3 CYCLOHEXANEDIONE; CARBOXYLIC ACID DERIVATIVE; CINCHONA ALKALOID; QUININE; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; HUMAN;

CINCHONA;

EID: 80755135407     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.040     Document Type: Article

References (53)

1. L. Bonsignore, G. Loy, D. Secci, and A. Calignano Eur. J. Med. Chem. 28 1993 517 520
2. Witte, E. C.; Neubert, P.; Roesch, A. Ger. Offen. DE 3427985, 1986; Chem. Abstr. 1986, 104, 224915.
3. L.L. Andreani, and E. Lapi Boll. Chim. Farm. 99 1960 583 586
4. R.W. DeSimone, K.S. Currie, S.A. Mitchell, J.W. Darrow, and D.A. Pippin Comb. Chem. High Throughput Screening 7 2004 473 494
5. D. Kumar, V.B. Reddy, S. Sharad, U. Dube, and S. Kapur Eur. J. Med. Chem. 44 2009 3805 3809
6. A. Anders, A.A. Jensen, M.N. Erichsen, C.W. Nielsen, T.B. Stensbøl, J. Jan Kehler, and L. Bunch J. Med. Chem. 52 2009 912 915
7. J.L. Wang, D. Liu, Z.J. Zhang, S. Shan, X. Han, S.M. Srinivasula, C.M. Croce, E.S. Alnemri, and Z. Huang Proc. Natl. Acad. Sci. U.S.A. 97 2000 7124 7129
8. N. Foloppe, L.M. Fisher, R. Howes, A. Potter, A.G.S. Robertson, and A.E. Surgenor Bioorg. Med. Chem. 14 2006 4792 4802
9. Z.H. Ismail, G.M. Aly, M.S. El-Degwi, H.I. Heiba, and M.M. Ghorab Egypt J. Biotechnol. 13 2003 73 82
10. M.E.A. Zaki, H.A. Soliman, O.A. Hiekal, and A.E. Rashad Z. Naturforsch. 61 2006 1 5
11. E.S. El-Tamany, F.A. El-Shahed, and B.H. Mohamed J. Serb. Chem. Soc. 64 1999 9 18
12. E.A.A. Hafez, M.H. Elnagdi, A.G.A. Elagamey, and F.M.A.A. Ei-Taweel Heterocycles 26 1987 903 907
13. Morinaka, Y.; Takahashi, K. Jpn. Kokai Tokkyo Koho JP52017498, 1977; Chem. Abstr. 1977, 87, 102299.
14. For examples of natural compounds containing the chromene moiety, see: W. Kemnitzer, J. Drewe, S.C. Jiang, H. Zhang, Y. Wang, J. Zhao, S. Jia, J. Herich, D. Labreque, R. Storer, K. Meerovitch, D. Bouffard, R. Rej, R. Denis, C. Blais, S. Lamothe, G. Attardo, H. Gourdeau, B. Tseng, S. Kasibhatla, and S.X. Cai J. Med. Chem. 47 2004 6299 6310
15. V.S. Parmar, S.C. Jain, K.S. Bisht, R. Jain, P. Taneja, A. Jha, O.D. Tyagi, A.K. Prasad, J. Wengel, C.E. Olsen, and P.M. Boll Phytochemistry 46 1997 597 674
16. M. Gill Aust. J. Chem. 48 1995 1 26
17. B.A. Bohm, J.B. Choy, and A.Y.-M. Lee Phytochemistry 28 1989 501 504
18. G.A. Iacobucci, and J.G. Sweeny Tetrahedron 39 1983 3005 3038
19. For a review, see: M.G. Núňez, P. García, R.F. Moro, and D. Díez Tetrahedron 66 2010 2089 2109
20. For selected examples, see: A.F.A. Harb, A.H.M. Hesien, S.A. Metwally, and M.H. Elnagdi Liebigs Ann. Chem. 1989 585 588
21. X.-S. Wang, J.-R. Wu, Q. Li, and S.-J. Tu J. Chem. Res. 2009 234 236
22. S.E. Zayed, E.I. Abou Elmaged, S.A. Metwally, and M.H. Elnagdi Collect. Czech. Chem. Commun. 56 1991 2175 2182
23. R. Ballini, G. Bosica, M.L. Conforti, R. Maggi, A. Mazzacani, P. Righi, and G. Sartori Tetrahedron 57 2001 1395 1398
24. S. Abdolmohammadi, and S. Balalaie Tetrahedron Lett. 48 2007 3299 3303
25. S. Gao, C.H. Tsai, C. Tseng, and C.-F. Yao Tetrahedron 64 2008 9143 9149
26. J.M. Khurana, and S. Kumar Tetrahedron Lett. 50 2009 4125 4127
27. X.S. Wang, G.S. Yang, and G. Zhao Tetrahedron: Asymmetry 19 2008 709 714
28. X.-S. Wang, C.-W. Zheng, S.-L. Zhao, Z. Chai, G. Zhao, and G.-S. Yang Tetrahedron: Asymmetry 19 2009 2699 2704
29. J.W. Xie, X. Huang, L.P. Fan, D.C. Xu, X.S. Li, H. Su, and Y.H. Wen Adv. Synth. Catal. 351 2009 3077 3082
30. Q. Ren, W.-Y. Siau, Z. Du, K. Zhang, and J. Wang Chem. Eur. J. 17 2011 7781 7785
31. Z. Dong, X. Liu, J. Feng, M. Wang, L. Lin, and X. Feng Eur. J. Org. Chem. 2011 137 142
32. S. Gogoi, and C.-G. Zhao Tetrahedron Lett. 50 2009 2252 2255
33. D. Ding, and C.G. Zhao Tetrahedron Lett. 51 2010 1322 1325
34. S. Muramulla, and C.-G. Zhao Tetrahedron Lett. 52 2011 3905 3908
35. For some leading examples of chincona alkaloid-catalyzed tandem reactions, see: M.M. Biddle, M. Lin, and K.A. Scheidt J. Am. Chem. Soc. 129 2007 3830 3831
36. L.-S. Zu, J. Wang, H. Li, H.-X. Xie, W. Jiang, and W. Wang J. Am. Chem. Soc. 129 2007 1036 1037
37. B. Wang, F. Wu, Y. Wang, X. Liu, and L. Deng J. Am. Chem. Soc. 129 2007 768 769
38. Y. Wang, X.-F. Liu, and L. Deng J. Am. Chem. Soc. 128 2006 3928 3930
39. T. Dudding, A.M. Hafez, A.E. Taggi, T.R. Wagerle, and T. Lectka Org. Lett. 4 2002 387 390
40. For an excellent review on organocatalyzed tandem reactions, see: D. Enders, C. Grondal, and M.R.M. Hüttl Angew. Chem., Int. Ed. 46 2007 1570 1581
41. For selected examples of chiral bifunctional thiourea catalysis, see: M.S. Sigman, and E.N. Jacobsen J. Am. Chem. Soc. 120 1998 5315
42. M.S. Sigman, P. Vachal, and E. Jacobsen Angew. Chem. 112 2000 1336 Angew. Chem., Int. Ed. 2000, 39, 1279
43. P. Vachal, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 10012
44. T. Okino, Y. Hoashi, and Y. Takemoto J. Am. Chem. Soc. 125 2003 12672
45. T. Okino, Y. Hoashi, T. Furukawa, and Y.T.X. Xu J. Am. Chem. Soc. 127 2005 119
46. P.M. Pihko Angew. Chem. 116 2004 2110 Angew. Chem., Int. Ed. 2004, 43, 2062
47. Y. Takemoto Org. Biomol. Chem. 3 2005 4299
48. S.J. Connon Chem. Eur. J. 12 2006 5418
49. S.J. Zuend, P.C. Matthew, P.L. Mathieu, and E.N. Jacobsen Nature 461 2009 968
50. A. Peschiulli, B. Procuranti, C.J. Oconnor, and S.J. Connon Nat. Chem. 2 2010 380
51. S. Balalaie, M. Bararjanian, M. Sheikh-Ahmadi, S. Hekmat, and P. Salehi Synth. Commun. 37 2007 1097 1108
52. T. Okino, Y. Hoashi, and Y. Takemoto J. Am. Chem. Soc. 125 2003 12672 12673
53. Although the optical purity of the isolated product is stable when it is pure, subject it to a less stereoselective catalyst under the optimized reaction conditions also led to reduced ee value of the product.