A surprising solid-phase effect: Development of a recyclable 'traceless' linker system for reactions on solid support

Angewandte Chemie - International Edition

Volumn 37, Issue 24, 1999, Pages 3413-3415

  Bräse, Stefan ^a   Enders, Dieter ^a   Köbberling, Johannes ^a   Avemaria, Frank ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Arenes; Asymmetric synthesis; C C coupling; Solid phase synthesis; Triazenes

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON; TRIAZENE DERIVATIVE;

ARTICLE; AUTOMATION; CHEMICAL REACTION; SOLID STATE; SYNTHESIS;

EID: 0033521576     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981231)37:24<3413::AID-ANIE3413>3.0.CO;2-K     Document Type: Article

References (38)

1. a) E. M. Gordon, R.W. Barrett, W.J. Dower, S. P. Fodor, M. A. Gallop, J. Med. Chem. 1994, 37, 1385-1401
2. b) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555-600
3. c) J. S. Früchtel, G. Jung, Angew. Chem. 1996, 108, 19-46 Angew. Chem. Int. Ed. Engl. 1996, 35, 17-42
4. c) J. S. Früchtel, G. Jung, Angew. Chem. 1996, 108, 19-46 Angew. Chem. Int. Ed. Engl. 1996, 35, 17-42
5. d) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2437-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337
6. d) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2437-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337
7. e) P. H. H. Hermkens, H.C.J. Ottenheijm, D. Rees, Tetrahedron 1997, 53, 5643-5678
8. f) Combinatorial Peptide and Nonpeptide Libraries (Ed. : G. Jung), VCH, Weinheim, 1996;
9. g) Combinatorial Chemistry (Eds.: S. R. Wilson, A. W. Czarnik), Wiley-Interscience, New York, 1997, and references therein.
10. B.J. Backes, J. A. Ellman, Curr. Opin. Chem. Biol. 1997, 1, 86-93.
11. a) M. J. Plunkett, J. A. Ellman, J. Org. Chem. 1995, 60, 6006-6007
12. b) M. J. Plunkett, J. A. Ellman, J. Org. Chem. 1997, 62, 2885-2893;
13. c) B. Chenera, J. A. Finkelstein, D. F. Veber, J. Am. Chem. Soc. 1995, 117, 11999-12000
14. d) T. L. Boehm, H. D. Showalter, J. Org. Chem. 1996, 61, 6498-6499
15. e) A. Routledge, H. T. Stock, S. L. Flitsch, N. J. Turner, Tetrahedron Lett. 1997, 38, 8237-8290
16. f) M. Schuster, N. Lucas, S. Blechert, Chem. Commun. 1997, 823-824.
17. For a Pd-catalyzed "traceless" cleavage, see S. Jin, D. P. Holub, D. J. Wustrow, Tetrahedron Lett. 1998, 39, 3651.
18. a) For a "traceless linker" for isoquinolines, see B. A. Lorsbach, J. T. Bagdanoff, R. B. Miller, M. J. Kurth, J. Org. Chem. 1998, 63, 2244-2250
19. b) for a "linker" for amines, see X. Ouyang, R. W. Armstrong, M. M. Murphy, J. Org. Chem. 1998, 63, 1027-1032
20. c) for a photo-labile benzyl sulfide linker, see F. W. Forman, I. Sucholeiki, J. Org. Chem. 1995, 60, 523-528
21. d) for a "traceless linker" for carboxylic acids, see P. Garibay, J. Nielsen, T. Hoeg-Jensen, Tetrahedron Lett. 1998, 39, 2207-2210
22. e) P. Conti, D. Demont, J. Cals, H. C.J. Ottenheijm, D. Leysen, Tetrahedron Lett. 1997, 38, 2915-2918;
23. f) C. R. Johnson, B. Zhang, Tetrahedron Lett. 1995, 36, 9253-9256;
24. g) for the use of sulfones as linkers, see L. M. Gayo, M. J. Suto, Tetrahedron Lett. 1997, 38, 211-214
25. h) for the use of an aliphatic C-H "traceless" linker, see X. Zhao, K. W. Jung, K. D. Janda, Tetrahedron Lett. 1997, 38, 977-980; Tetrahedron Lett. 1997, 38, 6645-6652; K. W. Jung, X. Zhao, K. D. Janda, Tetrahedron Lett. 1996, 37, 6491-6494;
26. h) for the use of an aliphatic C-H "traceless" linker, see X. Zhao, K. W. Jung, K. D. Janda, Tetrahedron Lett. 1997, 38, 977-980; Tetrahedron Lett. 1997, 38, 6645-6652; K. W. Jung, X. Zhao, K. D. Janda, Tetrahedron Lett. 1996, 37, 6491-6494;
27. h) for the use of an aliphatic C-H "traceless" linker, see X. Zhao, K. W. Jung, K. D. Janda, Tetrahedron Lett. 1997, 38, 977-980; Tetrahedron Lett. 1997, 38, 6645-6652; K. W. Jung, X. Zhao, K. D. Janda, Tetrahedron Lett. 1996, 37, 6491-6494;
28. i) for further linkers, see I. Hughes, Tetrahedron Lett. 1996, 37, 7595-7598
29. j) R. Brown, D. C. Rees, Z. Rankovic, J. R. Morphy, J. Am. Chem. Soc. 1997, 119, 3288-3295
30. k) X. Zhao, K. D. Janda, Tetrahedron Lett. 1997, 38, 5437-5440
31. 1) S. W. Kim, S. Y. Ahn, J. S. Koh, J. H. Lee, S. R. Ro, H. Y. Cho, Tetrahedron Lett. 1997, 38, 4603-4606;
32. m) A. K. Szardenings, T. Burkoth, H. H. Lu, D. W. Tien, D. A. Campbell, Tetrahedron 1997, 53, 6573-6593
33. n) M. R. Gowravaram, M.A. Gallop, Tetrahedron Lett. 1997, 38, 6973-6976
34. o) A.D. Piscopio, J.F. Miller, K. Koch, Tetrahedron Lett. 1997, 38, 7143-7146
35. p) F. & K. Kroll, R. Morphy, D. Rees, D. Gani, Tetrahedron Lett. 1997, 38, 8573-8576
36. q) for cleavage by metathesis, see J. U. Peters, S. Blechert, Synlett 1997, 348-350
37. r) for an enzyme-labile linker, see B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190. Angew. Chem. Int. Ed. 1998, 37, 1143-1146.
38. r) for an enzyme-labile linker, see B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190. Angew. Chem. Int. Ed. 1998, 37, 1143-1146.