Methods for the synthesis of chiral sulfur heterocycles and their application in the asymmetric Baylis-Hillman reactions

Tetrahedron Asymmetry

Volumn 24, Issue 9-10, 2013, Pages 568-574

  Periasamy, Mariappan ^a   Gurubrahamam, Ramani ^a   Muthukumaragopal, Gopal P ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; MESYLIC ACID; SODIUM SULFIDE; SULFIDE; SULFUR DERIVATIVE; THIOPHENE; THIOPYRAN DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; BAYLIS HILLMAN REACTION; CHIRALITY; CYCLIZATION; ENANTIOMER; PRIORITY JOURNAL;

EID: 84877741713     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2013.03.021     Document Type: Article

References (37)

1. K. Julienne, and P. Metzner J. Org. Chem. 63 1998 4532 4534
2. V.K. Aggarwal, J.G. Ford, S. Fonquerna, H. Adams, R.V.H. Jones, and R. Fieldhouse J. Am. Chem. Soc. 120 1998 8328 8339
3. K. Julienne, P. Metzner, and V. Henryon J. Chem. Soc., Perkin Trans. 1 1999 731 735
4. J. Zanardi, C. Leriverend, D. Aubert, K. Julienne, and P. Metzner J. Org. Chem. 66 2001 5620 5623
5. M. Davoust, J.-F. Brière, and P. Metzner Org. Biomol. Chem. 4 2006 3048 3051
6. V.K. Aggarwal, E. Alonso, G. Fang, M. Ferrara, G. Hynd, and M. Porcelloni Angew. Chem., Int. Ed. 40 2001 1433 1436
7. V.K. Aggarwal, M. Ferrara, C.J. O'Brien, A. Thompson, R.V.H. Jones, and R. Fieldhouse J. Chem. Soc., Perkin Trans. 1 2001 1635 1643
8. O. Illa, M. Arshad, A. Ros, E.M. McGarrigle, and V.K. Aggarwal J. Am. Chem. Soc. 132 2010 1828 1830
9. V.K. Aggarwal, H.W. Smith, G. Hynd, R.V.H. Jones, R. Fieldhouse, and S.E. Spey J. Chem. Soc., Perkin Trans. 1 2000 3267 3276
10. V.K. Aggarwal, G.Y. Fang, and A.T. Schmidt J. Am. Chem. Soc. 127 2005 1642 1643
11. G.Y. Fang, O.A. Wallner, N.D. Blasio, X. Ginesta, J.N. Harvey, and V.K. Aggarwal J. Am. Chem. Soc. 129 2007 14632 14639
12. L.-Q. Lu, Z.-H. Ming, J. An, C. Li, J.-R. Chen, and W.-J. Xiao J. Org. Chem. 77 2012 1072 1080
13. For chiral sulfide directed reports, see: T. Iwama, S.-I. Tsujiyama, H. Kinoshita, K. Kanematsu, Y. Tsurukami, T. Iwamura, S.-I. Watanabe, and T. Kataoka Chem. Pharm. Bull. 47 1999 956 961
14. L.M. Walsh, C.L. Winn, and J.M. Goodman Tetrahedron Lett. 43 2002 8219 8222
15. E.L. Myers, J.G. De Vries, and V.K. Aggarwal Angew. Chem., Int. Ed. 46 2007 1893 1896
16. V.K. Aggarwal, I. Bae, H.-Y. Lee, J. Richardson, and D.T. Williams Angew. Chem., Int. Ed. 42 2003 3274 3278
17. V.K. Aggarwal, and J.-L. Vasse Org. Lett. 5 2003 3987 3990
18. G.Y. Fang, and V.K. Aggarwal Angew. Chem., Int. Ed. 46 2007 359 362
19. J. Bi, and V.K. Aggarwal Chem. Commun. 2008 120 122
20. M. Periasamy, G. Ramani, and G.P. Muthukumaragopal Synthesis 2009 1739 1743
21. D.J. Aldous, W.M. Dutton, and P.G. Steel Tetrahedron: Asymmetry 11 2000 2455 2462
22. F.J. Robertson, and J. Wu J. Am. Chem. Soc. 134 2012 2775 2780
23. M. Periasamy, N. Sanjeevakumar, M. Dalai, R. Gurubrahamam, and P.O. Reddy Org. Lett. 14 2012 2932 2935
24. E.J. Corey, R.K. Bakshi, S. Shibata, C.-P. Chen, and V.K. Singh J. Am. Chem. Soc. 109 1987 7925 7926
25. R. Downham, P.J. Edwards, D.A. Entwistle, A.B. Hughes, K.S. Kim, and S.V. Ley Tetrahedron: Asymmetry 6 1995 2403 2440
26. D. Basavaiah, P. Dharma Rao, and R.S. Hyma Tetrahedron 52 1996 8001 8062
27. D. Basavaiah, B.S. Reddy, and S.S. Badsara Chem. Rev. 110 2010 5447 5674
28. G. Masson, C. Housseman, and J. Zhu Angew. Chem., Int. Ed. 46 2007 4614 4628
29. J. Mansilla, and J.M. Saa Molecules 15 2010 709 734
30. For representative chalcogenide directed racemic reports, see: T. Kataoka, T. Iwama, S.-I. Tsujiyama, T. Iwamura, and S.-I. Watanabe Tetrahedron 54 1998 11813 11824
31. T. Iwama, H. Kinoshita, and T. Kataoka Tetrahedron Lett. 40 1999 3741 3744
32. M. Shi, and J.-K. Jiang Tetrahedron 56 2000 4793 4797
33. J.S. Rao, J.-F. Briere, P. Metzner, and D. Basavaiah Tetrahedron Lett. 47 2006 3553 3556
34. T. Oishi, H. Oguri, and M. Hirama Tetrahedron: Asymmetry 6 1995 1241 1244
35. K. Yuan, L. Zhang, H.-L. Song, Y. Hu, and X.-Y. Wu Tetrahedron Lett. 49 2008 6262 6264
36. J.K. Whitesell, and S.W. Felman J. Org. Chem. 42 1977 1663 1664
37. A. Kamal, M. Sandbhor, and A.A. Shaik Tetrahedron: Asymmetry 14 2003 1575 1580