Parallel synthesis of tandem Ugi/Diels-Alder reaction products on a soluble polymer support directed toward split-pool realization of a small molecule library

Tetrahedron Letters

Volumn 46, Issue 3, 2005, Pages 415-418

  Oikawa, Masato ^a   Ikoma, Minoru ^a   Sasaki, Makoto ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBOXYLIC ACID; POLYMER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DIELS ALDER REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 11144283645     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.115     Document Type: Article

References (32)

1. R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, and T.A. Keating Acc. Chem. Res. 29 1996 123 131
2. L. Weber, K. Illgen, and M. Almstetter Synlett 1999 366 374
3. H. Bienayme, C. Hulme, G. Oddon, and P. Schmitt Chem. Eur. J. 6 2000 3321 3329
4. A. Domling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3169 3210
5. A. Domling Curr. Opin. Chem. Biol. 4 2000 318 323
6. R.V.A. Orru, and M. de Greef Synthesis 2003 1471 1499
7. I. Ugi Angew. Chem., Int. Ed. Engl. 71 1959 386
8. P. Cristau, J.P. Vors, and J.P. Zhu Tetrahedron Lett. 44 2003 5575 5578
9. D. Naskar, A. Roy, W.L. Seibel, L. West, and D.E. Portlock Tetrahedron Lett. 44 2003 6297 6300
10. D.E. Portlock, D. Naskar, L. West, R. Ostaszewski, and J.J. Chen Tetrahedron Lett. 44 2003 5121 5124
11. D.E. Portlock, R. Ostaszewski, D. Naskar, and L. West Tetrahedron Lett. 44 2003 603 605
12. V. Gracias, J.D. Moore, and S.W. Djuric Tetrahedron Lett. 45 2004 417 420
13. K. Paulvannan Tetrahedron Lett. 40 1999 1851 1854
14. For intramolecular Diels-Alder reaction of furan, see; T. Mukaiyama, and N. Iwasawa Chem. Lett. 1981 29 32
15. J. Breu, T. Butz, K.J. Range, and Sauer Acta Cryst. C53 1997 515 517
16. C.O. Kappe, S.S. Murphree, and A. Padwa Tetrahedron 53 1997 14179 14233
17. F. Ghelfi, A.F. Parsons, D. Tommasini, and A. Mucci Eur. J. Org. Chem. 2001 1845 1852
18. D.L. Wright, C.V. Robotham, and K. Aboud Tetrahedron Lett. 43 2002 943 946
19. S. Akai, T. Naka, S. Omura, K. Tanimoto, M. Imanishi, Y. Takebe, M. Matsugi, and Y. Kita Chem. Eur. J. 8 2002 4255 4264
20. A tandem UDA reaction with pyrolle has been reported recently, see; K. Paulvannan J. Org. Chem. 69 2004 1207 1214
21. D.S. Lee, J.K. Sello, and S.L. Schreiber Org. Lett. 2 2000 709 712
22. J.K. Sello, P.R. Andreana, D.S. Lee, and S.L. Schreiber Org. Lett. 5 2003 4125 4127
23. MPEG-OH and TentaGel S OH resin were purchased from Aldrich Co. (catalog No. 20251-7) and Advanced ChemTech, Inc. (catalog No. SJ6004), respectively
24. M. Oikawa, T. Tanaka, S. Kusumoto, and M. Sasaki Tetrahedron Lett. 45 2004 787 790
25. For our related studies using another soluble polymer platform, MPEG-O-AAc-, for rather simple Ugi four-component coupling reaction, see: M. Oikawa, M. Ikoma, and M. Sasaki Tetrahedron Lett. 45 2004 2371 2375
26. 4,7 where no library has been realized yet for the tandem UDA product
27. 1H NMR spectra
28. 3)
29. The usefullness of this platform will be reported elsewhere
30. Since the loading of primary alcohols onto the resin proceeds approximately in 30% yield (data not shown), the yields for the tandem UDA and the cleavage reactions were evaluated to be 80% and >96%, respectively. The MTM group, after the loading, is supposed to be hydrolyzed and the generating hydroxy group is inert during the tandem UDA reaction followed by the cleavage. We are currently investigating a high-yield immobilization method for primary alcohols on the platform
31. S.L. Schreiber Science 287 2000 1964 1969
32. M.D. Burke, and S.L. Schreiber Angew. Chem., Int. Ed. 43 2004 46 58