Straightforward stereoselective synthesis of spiro-epoxyoxindoles

Organic Letters

Volumn 9, Issue 9, 2007, Pages 1745-1748

  Schulz, Verena ^a   Davoust, Marion ^a   Lemarié, Margareth ^a,b   Lohier, Jean François ^a,b   De Santos, Jana Sopkova Oliveira ^a,b,c   Metzner, Patrick ^a   Brière, Jean François ^a  

^a UNIVERSITÉ DE CAEN   (France)

^b Analytical Department   (France)

^c Centre d'Etude et de Recherche sur le Médicament de Normandie   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; INDOLE DERIVATIVE; N METHYLISATIN; N-METHYLISATIN; OXINDOLE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EPOXY COMPOUNDS; INDOLES; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 34248374439     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070439x     Document Type: Article

References (56)

1. For selected recent examples, see: (a) Nair, V.; Vellalath, S.; Poonoth, M.; Mohan, R.; Suresh, E. Org. Lett. 2006, 8, 507.
2. (b) Alcaide, B.; Almendros, P.; Rodriguez-Acebes, R. J. Org. Chem. 2006, 71, 2346.
3. (c) Suarez-Castillo, O. R.; Sanchez-Zavala, M.; Melendez-Rodriguez, M.; Castelan-Duarte, L. E.; Morales-Rios, M. S.; Joseph-Nathan, P. Tetrahedron 2006, 62, 3040.
4. (d) Kim, S. C.; Gowrisankar, S.; Kim, J. N. Tetrahedron Lett. 2006, 47, 3463.
5. For selected recent asymmetric examples, see: (a) Nakamura, T.; Shirokawa, S.; Hosokawa, S.; Nakazaki, A.; Kobayashi, S. Org. Lett. 2006, 8, 677.
6. (b) Chen, G.; Wang, Y.; He, H.; Gao, S.; Yang, X.; Hao, X. Heterocycles 2006, 68, 2327.
7. (c) Toullec, P. Y.; Jagt, R. B. C.; De Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Org. Lett. 2006, 8, 2715.
8. (d) Cravotto, G.; Giovenzana, G. B.; Palmisano, G.; Penoni, A.; Pilati, T.; Sisti, M.; Stazi, F. Tetrahedron: Asymmetry 2006, 17, 3070.
9. (e) Shintani, R.; Inoue, M.; Hayashi, T. Angew. Chem., Int. Ed. 2006, 45, 3353.
10. (f) Kawasaki, T.; Takamiya, W.; Okamoto, N.; Nagaoka, M.; Hirayama, T. Tetrahedron Lett. 2006, 47, 5379.
11. (g) Ishimaru, T.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.; Kanemasa, S. J. Am. Chem. Soc. 2006, 128, 16488.
12. (h) Franz, A. Z.; Dreyfuss, P. D.; Schreider, S. L. J. Am. Chem. Soc. 2007, 129, 1020.
13. (a) Anthony, W. C. U.S. Patent 3413299, 1968.
14. (b) Plostnieks, J. U.S. Patent 3397202, 1968.
15. (c) Kobayashi, G.; Matsuda, Y. Jpn. Tokkyo Koho Patent 42015542, 1967.
16. (d) Dandia, A.; Singh, R.; Saha, M.; Shivpuri, A. Pharmazie 2002, 57, 602 and references cited therein.
17. Marx, K. A.; O'Neil, P.; Huffman, P.; Ujwal, M. L. J. Chem. Inf. Comput. Sci. 2003, 43, 1652.
18. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209.
19. (a) Arndt, F.; Eistert, B.; Ender, W. Ber. Dtsch. Chem. Ges. 1929, 62B, 44.
20. (b) Schoenberg, A.; Junghans, K. Chem. Ber. 1963, 96, 3328.
21. (c) Capuano, L.; Welter, M. Chem. Ber. 1968, 101, 3671.
22. (d) Kennewell, P. D.; Miller, D. J.; Scrowston, R. M.; Westwood, R. J. Chem. Res., Synop. 1995, 396.
23. (e) Muthusamy, S.; Gunanathan, C.; Nethaji, M. Synlett 2004, 639.
24. (a) Ainley, A. D.; Robinson, R. J. Chem. Soc. 1934, 1508.
25. (b) Kikumoto, R.; Kobayashi, T. Tetrahedron 1966, 22, 3337.
26. (c) Baiocchi, L.; Giannangeli, M. J. Heterocycl. Chem. 1988, 25, 1905.
27. (d) Dandia, A.; Sachdeva, H.; Ahmed, N.; Joshi, K. C. Heterocycl. Commun. 2000, 6, 181.
28. (e) Nishizono, N.; Oda, K.; Kalo, Y.; Ohno, K.; Minami, M.; Machida, M. Heterocycles 2004, 63, 1083.
29. (a) Ager, J. W., Jr.; Eastwood, F. A.; Robinson, R. Tetrahedron, Supplement 1966, 7, 277.
30. (b) Anthony, W. C. J. Org. Chem. 1966, 31, 77.
31. (c) Kobayashi, G.; Matsuda, Y.; Tominaga, Y.; Ohkuma, M.; Shinoda, H.; Kohno, M.; Mizuno, D. Yakugaku Zasshi 1977, 97, 1033.
32. (d) Joshi, K. C.; Jain, R.; Garg, S. J. J. Heterocycl. Chem. 1984, 21, 977.
33. (e) Brunton, S. A.; Jones, K. J. Chem. Soc., Perkin Trans. 1 2000, 763.
34. To our knowledge, there is no enantioselective synthesis of epoxyoxindoles, although an asymmetric substrate-controlled diastereoselective epoxidation has been reported. See: Inoue, M.; Sakazaki, H.; Furukawa, H.; Hirama, M. Angew. Chem., Int. Ed. 2003, 42, 2654.
35. There is one example of isatin epoxidation by dimethysulfonium methylide having therefore no diastereoselective issue. See: Bravo, P.; Gaudiano, G.; Umani-Ronchi, A. Gazz. Chim. Ital. 1970, 100, 652.
36. For reviews, see: (a) Aggarwal, V. K.; Richardson, J. Chem. Commun. 2003, 2644.
37. (b) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
38. (c) Aggarwal, V. K.; Badine, D. M.; Moorthie, V. A. In Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, 2006; p 1.
39. For recent successful diastereo- and enantioselective sulfur ylide epoxidation of ketones, see: Aggarwal, V. K.; Bae, I.; Lee, H.-Y.; Richardson, J.; Williams, D. T. Angew. Chem., Int. Ed. 2003, 42, 3274.
40. Rats, K. W.; Yao, A. N. J. Org. Chem. 1966, 31, 1689.
41. (a) Fernández, M. V.; Durante-Lanes, P.; López-Herrera, F. J. Tetrahedron 1990, 46, 7911.
42. (b) Zhou, Y.-G.; Hou, X.-L.; Dai, L. X.; Xia, L. J.; Tang, M.-H. J. Chem. Soc., Perkin Trans. 1 1999, 77.
43. (c) Saito, T.; Akiba, D.; Sakairi, M.; Ishikawa, K.; Otani, T. Arkivoc 2004, ii, 152.
44. (d) Aggarwal, V. K.; Hebach, C. Org. Biomol. Chem. 2005, 3, 1419.
45. (e) Sarabia, F.; Sánchez-Rui, A.; Chammaa, S. Org. Biomol. Chem. 2005, 13, 1691.
46. (f) Aggarwal, V. K.; Charmant, J. P. H.; Fuentes, D.; Harvey, J. N.; Hynd, G.; Ohara, D.; Picoul, W.; Robiette, R.; Smith, C.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2006, 128, 2105 and references therein for background knowledge.
47. (a) Aggarwal, V. K.; Blackburn, P.; Fieldhouse, R.; Jones, R. V. H. Tetrahedron Lett. 1998, 39, 8517.
48. (b) Imashiro, R.; Yamanaka, T.; Seki, M. Tetrahedron: Asymmetry 1999, 10, 2845.
49. Arai, S.; Tokumaru, K.; Aoyama, T. Tetrahedron Lett. 2004, 45, 1845.
50. Anthony, W. C. J. Org. Chem. 1966, 31, 77.
51. 2O (9:1).
52. For in situ formation of sulfonium salts for ylide cyclopropanation chemistry, see: Rasmy, O. M.; Vaid, R. K.; Semo, M J.; Chelius, E. C.; Robey, R. L.; Alt, C. A.; Rhodes, G. A.; Vivenzi, J. T. Org. Process Res. Dev. 2006, 10, 28. See ref 14 for the the sulfonium salt isolation.
53. Meth-Cohn, O.; Chen, Y. Tetrahedron Lett. 1999, 40, 6069.
54. 1H NMR spectrum; however, according to the X-ray crystal structure, this is a trans-epoxide.
55. Recently, a related explanation was proposed to account for the diastereoselective sulfonium ylide cyclopropanation of 3-methylene oxindoles. See: Yong, S. R.; Ung, A. T.; Pyne, S. G.; Skelton, B. W.; White, A. H. Tetrahedron 2007, 63, 1191.
56. The (R,R)-2,5-dimethylthiolane afforded the (+)-epoxide 4a in similar enantioselectivities. For sulfide synthesis, see: Davoust, M.; Brière, J.-F.; Jaffrès, P.-A.; Metzner, P. J. Org. Chem. 2005, 70, 4166.