Thiol-mediated free radical cyclisations of isocyanides on solid support

Tetrahedron Letters

Volumn 45, Issue 46, 2004, Pages 8541-8543

  Lamberto, Massimiliano ^a   Corbett, David F ^b   Kilburn, Jeremy D ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; ETHANE; MERCAPTOETHANOL; POLYMER; PYROGLUTAMIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE; RESIN; THIOL;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

EID: 5644264941     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.078     Document Type: Article

References (32)

1. T. Saegusa, S. Kobayashi, and I. Yoshihiko J. Org. Chem. 35 1970 2118
2. M. Lamberto, D.F. Corbett, and J.D. Kilburn Tetrahedron Lett. 44 2003 1347
3. I. Lenoir, and M.L. Smith J. Chem. Soc., Perkin Trans. 1 2000 641
4. H. Josien, S.B. Ko, D. Bom, and D.P. Curran Chem. Eur. J. 4 1998 67
5. H. Josien, and D.P. Curran Tetrahedron 53 1997 8881
6. M.D. Bachi, and A. Melman J. Org. Chem. 62 1997 1896
7. M.D. Bachi, N. Bar-Ner, and A. Melman J. Org. Chem. 61 1996 7116
8. D.P. Curran, H. Liu, H. Josien, and S.B. Ko Tetrahedron 52 1996 11385
9. M.D. Bachi, and A. Melman J. Org. Chem. 60 1995 6242
10. D.P. Curran, S.B. Ko, and H. Josien Angew. Chem., Int. Ed. Engl. 34 1995 2683
11. M.D. Bachi, A. Balanov, and N. Bar-Ner J. Org. Chem. 59 1994 7752
12. T. Fukuyama, X. Chen, and G. Peng J. Am. Chem. Soc. 116 1994 3127
13. D.P. Curran, and H. Liu J. Am. Chem. Soc. 114 1992 5863
14. D.P. Curran, and H. Liu J. Am. Chem. Soc. 113 1991 2127
15. For a review, see: A. Ganesan Radical Reactions on Solid Support M. Sibi P. Renaud Radicals in Organic Synthesis 2000 Wiley-VCH
16. For recent examples, see also: H. Miyabe, A. Nishimura, Y. Fujishima, and T. Naito Tetrahedron 59 2003 1901
17. D.C. Harrowven, P.J. May, and M. Bradley Tetrahedron Lett. 44 2003 503
18. K.C. Nicolaou, A.J. Roecker, J.A. Pfefferkorn, and Cao Gou-Quiang J. Am. Chem. Soc. 122 2000 2966
19. H. Miyabe, Y. Fujishima, and T. Naito J. Org. Chem. 64 1999 2174
20. Y. Watanabe, S. Ishikawa, G. Takao, and T. Toru Tetrahedron Lett. 40 1999 3411
21. X. Zhu, and A. Ganesan J. Comb. Chem. 1 1999 157
22. 2O) of racemic allyl glycine: J.C. Sheean, and D.-D.H. Jang J. Am. Chem. Soc. 80 1958 1154
23. L.I. Krimen Org. Synth. 50 1988 8
24. 2)
25. 13C NMR, IR and HRMS
26. M.J. O'Donnell, C. Zhou, and W.L. Scott J. Am. Chem. Soc. 118 1996 6070
27. Wang resin was purchased from CN Biosciences (UK) Ltd (loading = 0.86 mmol/g)
28. M.J. O'Donnell, and R.L. Polt J. Org. Chem. 47 1982 2663
29. M.M. Murphy, J.R. Schullek, E.M. Gordon, and M.A. Gallop J. Am. Chem. Soc. 117 1995 7029
30. R. Schweisinger, J. Willaredt, H. Schlemper, M. Keller, D.L. Schmidt, and H. Fritz Chem. Ber. 127 1994 2435
31. D.L. Griffith, M.J. O'Donnell, R.S. Pottorf, W.L. Scott, and J.A. Porco Tetrahedron Lett. 38 1997 8821
32. HMBA-AM resin was purchased from CN Biosciences (UK) Ltd (loading = 1.16 mmol/g)