Domino reactions in water for the stereoselective synthesis of novel spiro dihydro-2′H-[indene-2,3′-thiophen]-1(3H)-ones with three contiguous stereocenters

Tetrahedron Letters

Volumn 54, Issue 48, 2013, Pages 6651-6655

  Vivek Kumar, Sundaravel ^a   Prasanna, Pitchaimani ^a   Perumal, Subbu ^a  

^a MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

(E) 2 (Aryl) 2,3 dihydro 1H inden 1 one; 1,4 Dithiane 2,5 diol; 2 (Aryl) 4 hydroxy 4 ,5 dihydro 2 H spiro indene 2,3 thiophen 1(3H) one; Domino reactions; Stereoselectivity

Indexed keywords

1,4 DITHIANE DERIVATIVE; ACETALDEHYDE; INDENE DERIVATIVE; SOLVENT; SPIRO DIHYDRO 2'H (INDENE 2,3' THIOPHEN) 1(3H) ONE DERIVATIVE; THIOPHENE DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG; WATER;

ALDOL REACTION; ARTICLE; CATALYST; CHEMICAL BOND; DIASTEREOISOMER; DRUG SYNTHESIS; GREEN CHEMISTRY; MICHAEL ADDITION; MOLECULAR DYNAMICS; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SOLVENT EFFECT; STEREOCHEMISTRY;

EID: 84886775669     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.09.123     Document Type: Article

References (54)

1. T.P. Begley Nat. Prod. Rep. 23 2006 15
2. T.R. Ward Chem. Eur. J. 11 2005 3798
3. C. Fernandez-Mejía J. Nutr. Biochem. 16 2005 424
4. J. Zempleni Annu. Rev. Nutr. 25 2005 175
5. E. Gallienne, M. Benazza, G. Demailly, J. Bolte, and M. Lemaire Tetrahedron 61 2005 4557
6. P.C.P. Page, H. Vahedi, K.J. Batchelor, S.J. Hindley, M. Edgar, and P. Beswick Synlett 7 2003 1022
7. J. Zempleni, S.S. Wijeratne, and Y.I. Hassan Biofactors 35 2009 36
8. L.S. Jeong, S.A. Choe, P. Gunaga, H.K. Kim, H.W. Lee, S.K. Lee, D.K. Tosh, A. Patel, K.K. Palaniappan, Z.-G. Gao, K.A. Jacobson, and H.R. Moon J. Med. Chem. 50 2007 3159
9. S. Mohan, K. Jayakanthan, R. Nasi, D.A. Kuntz, D.R. Rose, and B.M. Pinto Org. Lett. 12 2010 1088
10. M. Yoshikawa, T. Murakami, K. Yashiro, and H. Matsuda Chem. Pharm. Bull. 46 1998 1339
11. G. Tanabe, W. Xie, A. Ogawa, C. Cao, T. Minematsu, M. Yoshikawa, and O. Muraoka Bioorg. Med. Chem. Lett. 19 2009 2195
12. G. Tanabe, K. Yoshikai, T. Hatanaka, M. Yamamoto, Y. Shao, T. Minematsu, O. Muraoka, T. Wang, H. Matsudab, and M. Yoshikawa Bioorg. Med. Chem. 15 2007 3926
13. M. Yoshikawa, T. Murakami, H. Shimada, H. Matsuda, J. Yamahara, G. Tanabe, and O. Muraoka Tetrahedron Lett. 38 1997 8367
14. R. Nasi, B.O. Patrick, L. Sim, D.R. Rose, and B.M. Pinto J. Org. Chem. 73 2008 6172
15. C. Qiao, K.Q. Ling, E.M. Shepard, D.M. Dooley, and L.M. Sayre J. Am. Chem. Soc. 128 2006 6206
16. Chorghade, M. S.; Gurjar, M. K.; Palakodety, R. K.; Lalitha, S. V. S.; Sadalapure, K.; Adhikari, S. S.; Murugaiah, A. M. S.; Rao, B. V.; Talukdar, A.; Islam, A.; Hariprasad, C.; Rao, A. V. R. Patent Application WO 1999-US15050, CAN 132:93203; 1999.
17. H.R. Moon, H.K. Kim, S.K. Lee, W.J. Choi, M.W. Chunc, and L.S. Jeong Bioorg. Med. Chem. 10 2002 1499
18. W. Zhu, Y. Chong, H. Choo, J. Mathews, R.F. Schinazi, and C.K. Chu J. Med. Chem. 47 2004 1631
19. K. Haraguchi, H. Shimada, H. Tanaka, T. Hamasaki, M. Baba, E.A. Gullen, G.E. Dutschman, and Y.-C. Cheng J. Med. Chem. 51 2008 1885
20. R.A. Volkmann, P.R. Kelbaugh, D.M. Nason, and V.J. Jasys J. Org. Chem. 57 1992 4352
21. Kato, T.; Tsuzuki, K. Patent Application JP 1992-147881, CAN 120: 106750; 1992.
22. V.A. Tsygoanko, and Y.B. Blume Biopolim. Kletka. 13 1997 484
23. D.R. Williams, P.A. Jass, H.L.A. Tse, and R.D. Gaston J. Am. Chem. Soc. 112 1990 4552
24. T. Mukaiyama, H. Asanuma, I. Hachiya, T. Harada, and S. Kobayashi Chem. Lett. 7 1991 1209
25. E. Hauptman, R. Shapiro, and W. Marshall Organometallics 17 1998 4976
26. J. Zanardi, D. Lamazure, S. Minière, V. Reboul, and P. Metzner J. Org. Chem. 67 2002 9083
27. J. Zanardi, C. Leriverend, D. Aubert, K. Julienne, and P. Metzner J. Org. Chem. 66 2001 5620
28. K. Julienne, P. Metzner, and V. Henryon J. Chem. Soc., Perkin Trans. 1 1999 731
29. K. Julienne, P. Metzner, V. Henryon, and A. Greirer J. Org. Chem. 63 1998 4532
30. A.-H. Li, L.-X. Dai, X.-L. Hou, Y.-Z. Huang, and F.-W. Li J. Org. Chem. 61 1996 489
31. H. Satoh, Y. Yoshimura, S. Sakata, S. Miura, H. Machida, and A. Matsuda Bioorg. Med. Chem. Lett. 8 1998 989
32. T. Ohtsuka, H. Kotaki, N. Nakayama, Y. Itezono, N. Shimma, T. Kudoh, T. Kuwahara, M. Arisawa, K. Yokose, and H. Seto J. Antibiot. 46 1993 11
33. S. Dong, and L.A. Paquette J. Org. Chem. 70 2005 1580
34. K.B. Szwed, J. Grochowski, A. Obara, B. Rys, and P. Serda J. Org. Chem. 66 2001 7205
35. K.B. Szwed, and R. Gil Monatsh. Chem. 135 2004 1415
36. K.B. Szwed, A. Budzowski, R. Gil, and P. Serda Monatsh. Chem. 141 2010 63
37. H. Giera, R. Huisgen, E. Langhals, and K. Polborn Helv. Chim. Acta 85 2002 1523
38. R. Huisgen, H. Giera, and K. Polborn Tetrahedron 61 2005 6143
39. S.W. Duan, Y. Li, Y.Y. Liu, Y.Q. Zou, D.Q. Shi, and W.J. Xiao Chem. Commun. 48 2012 5160
40. V.A. D́yakonov, O.A. Trapeznikova, A.G. Ibragimov, and U.M. Dzhemilev Russ. Chem. Bull., Int. Ed. 58 2009 948
41. V.A. D́yakonov, A.G. Ibragimov, L.M. Khalilov, A.A. Makarov, R.K. Timerkhanov, R.A. Tuktarova, O.A. Trapeznikova, and L.F. Galimova Chem. Heterocycl. Compd. 45 2009 317
42. For selected recent examples, see: P. Prasanna, S. Perumal, and J.C. Menendez Green Chem. 15 2013 1292
43. P. Gunasekaran, S. Indumathi, and S. Perumal RSC Adv. 3 2013 8318
44. S. Muthusaravanan, B. Devi Bala, and S. Perumal Tetrahedron Lett. 54 2013 5302
45. S. Indumathi, S. Perumal, and N. Anbanandan Green Chem. 14 2012 3361
46. B. Devi Bala, S. Michael Rajesh, and S. Perumal Green Chem. 14 2012 2484
47. S. Michael Rajesh, B. Devi Bala, S. Perumal, and J.C. Menéndez Green Chem. 13 2011 3248
48. S. Indumathi, S. Perumal, and J.C. Menéndez J. Org. Chem. 75 2010 472
49. U.M. Lindström Chem. Rev. 102 2002 2751
50. V.K. Ahluwalia, and R.S. Varma Green Solvents for Organic Synthesis 2009 Alpha Science International Abingdon, UK
51. Crystallographic data (excluding structure factors) for 3a (major) and 3i (minor) in this Letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 943561 and CCDC 947969 respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ].
52. For the first discussion of the 'on-water reaction' concept, see: S. Narayan, J. Muldoon, M.G. Finn, V.V. Fokin, H.C. Kolb, and K.B. Sharpless Angew. Chem., Int. Ed. 44 2005 3275
53. For reviews, see: A. Chanda, and V.V. Fokin Chem. Rev. 109 2009 725
54. R.N. Butler, and A.G. Coyne Chem. Rev. 110 2010 6302