Highly efficient solid-phase oxidative cleavage of olefins by OsO 4-NaIO4 in the intramolecular N-acyliminium Pictet-Spengler reaction

Organic Letters

Volumn 7, Issue 13, 2005, Pages 2695-2698

  Nielsen, Thomas E ^a   Meldal, Morten ^a  

^a CARLSBERG LABORATORY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; DRUG DERIVATIVE; FUSED HETEROCYCLIC RINGS; GLYCINE; ISOQUINOLINE DERIVATIVE; OSMIUM TETRAOXIDE; PYRROLE DERIVATIVE; SODIUM IODIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALDEHYDES; ALKENES; COMBINATORIAL CHEMISTRY TECHNIQUES; GLYCINE; HETEROCYCLIC COMPOUNDS, 3-RING; ISOQUINOLINES; MOLECULAR STRUCTURE; OSMIUM TETROXIDE; OXIDATION-REDUCTION; PYRROLES; SODIUM IODIDE;

EID: 26844432234     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050870r     Document Type: Article

References (47)

1. For an overview see: Dörwald, F. Z. Organic Synthesis on Solid Phase. Supports, Linkers, Reactions; Wiley-VCH: Weinheim, 2002; Chapter 12.
2. Selected examples: (a) Chen, C.; Randall, L. A. A.; Miller, R. B.; Jones, A. D.; Kurth, M. J. J. Am. Chem. Soc. 1994, 116, 2661-2662.
3. (b) Rotella, D. P. J. Am. Chem. Soc. 1996, 118, 12246-12247.
4. (c) Chen, C.; Randall, L. A. A.; Miller, R. B.; Jones, A. D.; Kurth, M. J. Tetrahedron 1997, 53, 6595-6609.
5. (d) Page, P.; Bradley, M. J. Org. Chem. 1999, 64, 794-799.
6. (e) Conde-Frieboes, K.; Schjeltved, R. K.; Breinholt, J. J. Org. Chem. 2002, 67, 8952-8957.
7. Marx, M. A.; Grillot, A.-L.; Louer, C. T.; Beaver, K. A.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6153-6167.
8. (a) Yan, B.; Sun, Q.; Wareing, J. R.; Jewell, C. F. J. Org. Chem. 1996, 61, 8765-8770.
9. (b) Li, W.; Yan, B. J. Org. Chem. 1998, 63, 4092-4097.
10. (a) Reggelin, M.; Brenig, V.; Welcker, R. Tetrahedron Lett. 1998, 39, 4801-4804.
11. (b) Nicolaou, K. C.; Pastor, J.; Winssinger, N.; Murphy, F. J. Am. Chem. Soc. 1998, 120, 5132-5133.
12. (c) Bang, J. K.; Hasegawa, K.; Kawakami, T.; Aimoto, S.; Akaji, K. Tetrahedron Lett. 2004, 45, 99-102.
13. Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 37, 6851-6852.
14. Veerman, J. J. N.; van Maarseveen, J. H.; Visser, G. M.; Kruse, C. G.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 1998, 2583-2589.
15. (a) Johannesson, P.; Lindeberg, G.; Tong, W.; Gogoll, A.; Karlén, A.; Hallberg, A. J. Med. Chem. 1999, 42, 601-608.
16. (b) Johannesson, P.; Lindeberg, G.; Tong, W.; Gogoll, A.; Synnergren, B.; Nyberg, F.; Karlén, A.; Hallberg, A. J. Med. Chem. 1999, 42, 4524-4537.
17. (c) Johannesson, P.; Erdélyi, M.; Lindeberg, G.; Frändberg, P.-A.; Nyberg, F.; Karlén, A.; Hallberg, A. J. Med. Chem. 2004, 47, 6009-6019.
18. (a) Sar, S.; Melnyk, O. Tetrahedron Lett. 2004, 45, 1271-1273.
19. (b) Sar, S.; Melnyk, O. Tetrahedron Lett. 2004, 45, 7163-7165.
20. (a) Groth, T.; Meldal, M. J. Comb. Chem. 2001, 3, 34-44.
21. (b) Groth, T.; Meldal, M. J. Comb. Chem. 2001, 3, 45-63.
22. (a) Schlienger, N.; Bryce, M. R.; Hansen, T. K. Tetrahedron Lett. 2000, 41, 5147-5150.
23. (b) Kobayashi, S.; Akiyama, R.; Kitagawa, H. J. Comb. Chem. 2001, 3, 196-204.
24. Rademann, J.; Meldal, M.; Bock, K. Chem. Eur. J. 1999, 5, 1218-1225.
25. Pappo, R.; Allen, D. S., Jr.; Lemieux, R. U.; Johnson, W. S. J. Org. Chem. 1956, 21, 478-479.
26. For Os-mediated dihydroxylation on solid support, see: (a) Cernerud, M.; Reina, J. A.; Tegenfeldt, J.; Moberg, C. Tetrahedron: Asymmetry 1996, 7, 2863-2870.
27. (b) Han, H.; Janda, K. D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1731-1733.
28. (c) Riedl, R.; Tappe, R.; Berkessel, A. J. Am. Chem. Soc. 1998, 120, 8994-9000.
29. (d) Bräse, S.; Enders, D.; Köbberling, J.; Avemaria, F. Angew. Chem., Int. Ed. 1998, 37, 3413-3415.
30. (e) Xia, Y.; Yang, Z.-Y.; Brossi, A.; Lee, K.-H. Org. Lett. 1999, 1, 2113-2115.
31. (f) Bräse, S.; Dahmen, S.; Pfefferkorn, M. J. Comb. Chem. 2000, 2, 710-715.
32. 4-mediated oxidative cleavage has been carried out on solid support to obtain a glyoxylyl- functionalized resin: Xu, Q.; Lam, K. S. Tetrahedron Lett. 2002, 43, 4435-4437.
33. Yu, W.; Mei, Y.; Kang, Y.; Hua, Z.; Jin, Z. Org. Lett. 2004, 6, 3217-3219.
34. (a) Nielsen, T. E.; Meldal, M. J. Org. Chem. 2004, 69, 3765-3773.
35. (b) Nielsen, T. E.; Meldal, M. J. Comb. Chem. 2005, submitted.
36. For solid-phase N-acyliminium Piclet-Spengler reactions, see also: (a) Wang, H.; Ganesan, A. Org. Lett. 1999, 1, 1647-1649.
37. (b) Bonnet, D.; Ganesan, A. J. Comb. Chem. 2002, 4, 546-548.
38. Selected examples: (a) Baldwin, J. E.; Freeman, R. T.; Schofield, C. Tetrahedron Lett. 1989, 30, 4019-4020.
39. (b) Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992, 114, 8778-8783.
40. (c) Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J. Tetrahedron Lett. 1993, 34, 1665-1668.
41. (d) Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Comun. 1993, 935-936.
42. (e) Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
43. (f) Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987.
44. (g) Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148.
45. (h) Ndungu, J. M.; Gu, X.; Gross, D. E.; Ying, J.; Hruby, V. J. Tetrahedron Lett. 2004, 45, 3245-3247.
46. For a recent review on turn mimics, see: Maison, W. In Highlights in Bioorganic Chemistry; Schmuck, C., Wennemers, H., Eds.; Wiley-VCH: Weinheim, 2004; Chapter 1.2, 18-29.
47. 3CN. The resulting solution was filtered through a Teflon filter and analyzed by RP-HPLC and ESMS.