Synthesis of 2,3,4-trisubstituted thiochromanes using an organocatalytic enantioselective tandem michael-henry reaction

Advanced Synthesis and Catalysis

Volumn 350, Issue 4, 2008, Pages 537-541

  Dodda, Rajasekhar ^a   Goldman, Joshua J ^a   Mandal, Tanmay ^a   Zhao, Cong Gui ^a   Broker, Grant A ^a   Tiekink, Edward R T ^a  

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

Author keywords

nitrostyrene; 2 mercaptobenzaldehyde; Henry reaction; Michael addition; Organocatalysis; Tandem reaction

Indexed keywords

EID: 47949088604     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700331     Document Type: Article

References (53)

1. For a review on chromanes and tocopherols, see: R. M. Parkhurst, W. A. Skinner, in: Chromanes and Tocopherols in Chemistry of Hererocyclic Compounds, (Ed.: G. P. Ellis, I. M. Lockhardt), Vol. 36, Wiley, New York, 1981, pp 1-469.
2. a) M. E. Castro, P. J. Harrison, A. Pazos, T. Sharp, T, J. Neurochem. 2000, 75, 755-762;
3. b) F. Lejuene, J.-M. Rivet, A. Gobert, H. Canton, M. J. Millan, Eur. J. Pharmacol. 1993, 240, 307-310;
4. c) M. L. Bolognesi, M. Bortolini, A. Cavalli, V. Andrisano, M. Rosini, A. Minarini, C. J. Melchiorre, J. Med. Chem. 2004, 47, 5945-5952;
5. d) L. A. V. Vliet, N. Rodenhuis, D. Dijkstra, H. Wikstrom, T. A. Pugsley, K. A. Serpa, L. T. Meltzer, T. G. Heffner, L. D. Wise, M. E. Lajiness, R. M. Huff, K. Svensson, S. Sundell, M. Lundmark, J. Med. Chem. 2000, 43, 2871-2882;
6. e) Y. Chen, Q. Zhang, B. Zhang, P. Xia, Y. Xia, Z.-Y. Yang, N. Kilgore, C. Wild, S. L. Morris-Natschka, K.-H. Lee, Bioorg. Med. Chem. 2004, 12, 6383-6387;
7. f) L. W. Spruce, S. N. Rajadhyaksha, K. D. Berlin, J. B. Gale, E. T. Miranda, W. T. Ford, E. C. Blossey, A. K. Verma, M. B. Hossain, D. V. D. Helm, T. R. Breitman, J. Med. Chem. 1987, 30, 1474-1482.
8. a) C. V. Ursini, G. H. M. Dias, J. A. R. Rodrigues, J. Organomet. Chem. 2005, 690, 3176-3186;
9. b) K. Micskei, C. Hajdu, L. A. Wessjohann, L. Mercs, A. Kiss-Szikszai, T. Patonay, Tetrahedron: Asymmetry 2004, 15, 1735-1744;
10. c) D. A. Evans, F. E. Michael, J. S. Tedrow, K. R. Campos, J. Am. Chem. Soc. 2003, 125, 3534-3543;
11. d) X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318-3319;
12. e) G. J. Quallich, T. M. Woodall, Tetrahedron Lett. 1993, 34, 785-788.
13. a) H. L. Holland, T. S. Manoharan, F. Schweizer, Tetrahedron: Asymmetry 1991, 2, 335-338;
14. b) H. Honig, N. Shi, G. Polanz, Biocatalysis 1994, 9, 61-69.
15. a) J.-W. Xie, W. Chen, R. Li, M. Zheng, W. Du, L. Yue, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. 2007, 119, 393-396;
16. Angew. Chem. Int. Ed. 2007, 46, 389-392;
17. b) D. Xue, Y.-C. Chen, Q.-W. Wang, L.-F. Cun, J. Zhu, J.-G. Deng, Org. Lett. 2005, 7, 5293-5296.
18. W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc. 2006, 128, 10354-10355.
19. See also: R. Rios, H. Sunden, I. Ibrahem, G.-L. Zhao, A. Cordova, Tetrahedron Lett. 2006, 47, 8679-8682.
20. L. Zu, J. Wang, H. Li, H. Xie, W. Jiang, W. Wang, J. Am. Chem. Soc. 2007, 129, 1036-1037.
21. a) S. Samata, J. Liu, R. Dodda, C.-G. Zhao, Org. Lett. 2005, 7, 5321-5323;
22. b) S. Samata, C.-G. Zhao, J. Am. Chem. Soc. 2006, 128, 7442-7443;
23. c) R. Dodda, C.-G. Zhao, Org. Lett. 2006, 8, 4911-4914;
24. d) S. Samanta, J. Krause, T. Mandal, C.-G. Zhao, Org. Lett. 2007, 9. 943-945.
25. For reviews, see: a) T. Ooi, K. Maruoka, K. Acc. Chem. Res. 2004, 37, 526-533;
26. b) C. Palomo, M. Oiarbide, A. Mielgo, Angew. Chem. 2004, 116, 5558-5560;
27. Angew. Chem. Int. Ed. 2004, 43, 5442-5444;
28. c) T. Marcelli, J. H. van Maarseveen, H. Hiemstra, Angew. Chem. 2006, 118, 7658-7666;
29. Angew. Chem. Int. Ed. 2006, 45, 7496-7504.
30. T. Mandal, S. Samanta, C.-G. Zhao, Org. Lett. 2007, 9, 943-945.
31. For selected examples on organocatalytic tandem reactions, see; a) D. B. Ramachary, N. S. Chowdari, C. F. Barbas, III. Angew. Chem. 2003, 115, 4365-4369;
32. Angew. Chem. Int. Ed. 2003, 42, 4233-4237;
33. b) Y. Yamamoto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5962-5963;
34. c) S. Brandau, E. Maerten, K. A. Jorgensen, J. Am. Chem. Soc. 2006, 128, 14986-14991;
35. d) D. Enders, M. R. M. Huttl, C. Grondal, G. Raabe, Nature 2006, 441, 861-863;
36. e) B. E. Maki, A. Chan, E. M. Phillips, K. A. Scheidt, Org. Lett. 2007, 9, 371-374;
37. f) S. Kotkar, V. B. Chavan, B. Vilas, A. Sudalai, Org. Lett. 2007, 9, 1001-1004;
38. g) H. Li, J. Wang, T. E-Nunu, L. Zu, W. Jiang, S. Wei, W. Wang, Chem. Commun. 2007, 507-509.
39. For reviews on tandem reactions, see: h) K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292-7344;
40. Angew. Chem. Int. Ed. 2006, 45, 7134-7186;
41. i) H.-C. Guo, J.-A. Ma, Angew. Chem. 2006, 118, 362-375;
42. Angew. Chem. Int. Ed. 2006, 45, 354-366;
43. j) L. F. Tietze, Chem. Rev. 1996, 96, 115-136.
44. a) A. Barco, N. Baricordi, S. Benetti, C. D. Risi, G. P. Pollini, Tetrahedron Lett. 2006, 47, 8087-8090;
45. b) R. Ballini, L. Barboni, D. Fiorini, G. Giarlo, A. Palmieri, Green Chem. 2005, 7, 828-829;
46. c) A. Barco, S. Benetti, C. D. Risi, G. P. Pollini, R. Romagnoli, V. Zanirato, Tetrahedron Lett. 1996, 37, 7599-7602;
47. d) A. Barco, S. Benetti, C. D. Risi, G. P. Pollini, R. Romagnoli, V. Zanirato, Tetrahedron Lett. 1994, 35, 9293-9296;
48. e) G. H. Posner, R. D. Crouch, Tetrahedron 1990, 46, 7509-7530.
49. Y. Hayashi, T. Okano, S. Arataka, D. Hazelard, Angew. Chem. 2007, 119, 5010-5013;
50. Angew. Chem. Int. Ed. 2007, 46, 4922-4925.
51. For a related example, see: C.-F. Yao, Y.-J. Jang, M.-C. Yan, Tetrahedron Lett. 2003, 44, 3813-3816.
52. 2-Mercaptobenzaldehydes were synthesized using a modified procedure originally reported by: T. Gallagher, D. A. Pardoe, R. A. Porter, Tetrahedron Lett. 2000, 41, 5415-5418.
53. For details, see Supporting Information.