An engineered linker capable of promoting on-resin reactions for microwave-assisted solid-phase organic synthesis

Angewandte Chemie - International Edition

Volumn 45, Issue 43, 2006, Pages 7255-7258

  Sun, Li Ping ^a   Dai, Wei Min ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

Heteroannulation; Heterocycles; Heterogeneous catalysis; Microwave assisted reactions; Solid phase synthesis

Indexed keywords

CATALYSIS; MICROWAVES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

HETEROANNULATION; HETEROCYCLES; MICROWAVE ASSISTED REACTIONS; SOLID PHASE SYNTHESIS;

RESINS;

EID: 33751012441     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602523     Document Type: Article

References (42)

1. a) F. Zaragoza Dörwald, Organic Synthesis on Solid Phase. Supports, Linkers, Reactions, Wiley-VCH, Weinheim, 2000;
2. b) Solid-Phase Organic Synthesis (Ed.: K. Burgess), Wiley-Interscience, New York, 2000;
3. c) P. Seneci, Solid-Phase Synthesis and Combinatorial Technologies, Wiley-Interscience, New York, 2000;
4. d) S. Bräse, J. H. Kirchhoff, J. Köbberling, Tetrahedron 2003, 59, 885-939.
5. a) Handbook of Combinatorial Chemistry (Eds.: K. C. Nicolaou, R. Hanko, W. Hartwig), Wiley-VCH, Weinheim, 2002;
6. b) Combinatorial Chemistry. A Practical Approach (Eds.: W. Bannwarth, E. Felder), Wiley-VCH, Weinheim, 2000;
7. c) Combinatorial Chemistry. Synthesis, Analysis, Screening (Ed.: G. Jung), Wiley-VCH, Weinheim, 1999.
8. F. Guillier, D. Orain, M. Bradley, Chem. Rev. 2000, 100, 2091-2157.
9. a) A. C. Comely, S. E. Gibson, Angew. Chem. 2001, 113, 1042-1063;
10. Angew. Chem. Int. Ed. 2001, 40, 1012-1032;
11. b) C. W. Phoon, M. M. Sim, Curr. Org. Chem. 2002, 6, 937-964;
12. c) P. Blaney, R. Grigg, V. Sridharan, Chem. Rev. 2002, 102, 2607-2624;
13. d) A. J. Wills, S. Balasubramanian, Curr. Opin. Chem. Biol. 2003, 7, 346-352;
14. e) S. Bräse, Acc. Chem. Res. 2004, 37, 805-816;
15. f) C. Gil, S. Bräse, Curr. Opin. Chem. Biol. 2004, 8, 230-237.
16. a) C. W. Y. Chung, P. H. Toy, Tetrahedron: Asymmetry 2004, 15, 387-399;
17. b) Y. Zhang, Y. Wang, W.-M. Dai, J. Org. Chem. 2006, 71, 2445-2455, and references therein.
18. a) N. E. Leadbeater, M. Marco, Chem. Rev. 2002, 102, 3217-3274;
19. b) C. A. McNamara, M. J. Dixon, M. Bradley, Chem. Rev. 2002, 102, 3275-3300.
20. The results are taken in part from L.-P. Sun, PhD thesis, The Hong Kong University of Science and Technology (P.R. China), 2004.
21. W.-M. Dai, D.-S. Guo, L.-P. Sun, X.-H. Huang, Org. Lett. 2003, 5, 2919-2922.
22. B. C. J. van Esseveldt, F. L. van Delft, R. de Gelder, F. P. J. T. Rutjes, Org. Lett. 2003, 5, 1717-1720, and references therein.
23. a) M. G. Saulnier, D. B. Frennesson, M. S. Deshpande, D. M. Vyas, Tetrahedron Lett. 1995, 36, 7841-7844;
24. b) K. Hiroya, S. Itoh, M. Ozawa, Y. Kanamori, T. Sakamoto, Tetrahedron Lett. 2002, 43, 1277-1280;
25. c) K. Hiroya, S. Itoh, T. Sakamoto, J. Org. Chem. 2004, 69, 1126-1136.
26. a) M. Nüchter, B. Ondruschka, W. Bonrath, A. Gum, Green Chem. 2004, 6, 128-141;
27. b) C. O. Kappe, Angew. Chem. 2004, 116, 6408-6443;
28. Angew. Chem. Int. Ed. 2004, 43, 6250-6284;
29. c) C. O. Kappe, A. Stadler, Microwaves in Organic and Medicinal Chemistry, Wiley-VCH, Weinheim, 2005.
30. a) W.-M. Dai, D.-S. Guo, L.-P. Sun, Tetrahedron Lett. 2001, 42, 5275-5278;
31. b) W.-M. Dai, L.-P. Sun, D.-S. Guo, Tetrahedron Lett. 2002, 43, 7699-7702;
32. c) L.-P. Sun, X.-H. Huang, W.-M. Dai, Tetrahedron 2004, 60, 10 983-10 992, and references therein.
33. For an example of intramolecular imide formation from a resin-bound succinic acid monoamide, see: F. Stieber, U. Grether, H. Waldmann, Chem. Eur. J. 2003, 9, 3270-3281.
34. H. J. Olivos, P. G. Alluri, M. M. Reddy, D. Salony, T. Kodadek, Org. Lett. 2002, 4, 4057-4059.
35. II with polypeptides such as polyglycines requires an efficient anchoring donor and involves the amide nitrogen atom, thereby resulting in facile amide deprotonation; see: a) H. Sigel, R. B. Martin, Chem. Rev. 1982, 82, 385-426;
36. b) K.-E. Falk, H. C. Greeman, T. Jansson, B. G. Malmstrom, T. Vanngard, J. Am. Chem. Soc. 1967, 89, 6071-6077;
37. c) M. P. Youngblood, K. L. Chellappa, C. E. Bannister, D. W. Margerum, Inorg. Chem. 1981, 20, 1742-1747;
38. II complexes bound through amide oxygen atoms have been reported; see reference [16].
39. a) J. C. Pessoa, I. Correia, T. Kiss, T. Jakusch, M. M. C. A. Castro, C. G. G. C. Geraldes, J. Chem. Soc. Dalton Trans. 2002, 4440-4450;
40. b) Y. Rodríguez-Martín, P. A. L. Luis, C. Ruiz-Pérez, Inorg. Chim. Acta 2002, 328, 169-178;
41. c) K. B. Girma, V. Lorenz, S. Blaurock, F. T. Edelmann, Inorg. Chim. Acta 2006, 359, 364-368.
42. The LC-MS charts can be found in the Supporting Information.