Application of 7-endo, 8-endo and 9-endo radical cyclisations to the synthesis of conformationally constrained amino acids and comparison with the corresponding Heck reactions

Chemical Communications

Volumn , Issue 6, 1997, Pages 637-638

  Gibson, Susan E ^a   Guillo, Nathalie ^a   Tozer, Matthew J ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b James Black Foundation   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542426509     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

1. (a) B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K. J. Kulicka and F. Trach, Org. React. (N.Y.), 1996, 48, 315;
2. (b) W. B. Motherwell and D. Crich, Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1992, p. 242;
3. (c) A. L. J. Beckwith and C. H. Schiesser, Tetrahedron, 1985, 41, 3925.
4. For recent examples, see (a) L. Colombo, M. Di Giacomo, G. Papeo, O. Caringo, C. Scolastico and L. Manzoni, Tetrahedron Lett., 1994, 35, 4031; (b) C. D. S. Brown, A. P. Dishington, O. Shishkin and N. S. Slmpkins, Synlett, 1995, 943; (c) C. J. Moody and C. L. Norton, Tetrahedron Lett., 1995, 36, 9051; (d) A. K. Mohanakrishnan and P. C. Srinivasan, Tetrahedron Lett., 1996, 37, 2659.
5. For recent examples, see (a) L. Colombo, M. Di Giacomo, G. Papeo, O. Caringo, C. Scolastico and L. Manzoni, Tetrahedron Lett., 1994, 35, 4031; (b) C. D. S. Brown, A. P. Dishington, O. Shishkin and N. S. Slmpkins, Synlett, 1995, 943; (c) C. J. Moody and C. L. Norton, Tetrahedron Lett., 1995, 36, 9051; (d) A. K. Mohanakrishnan and P. C. Srinivasan, Tetrahedron Lett., 1996, 37, 2659.
6. For recent examples, see (a) L. Colombo, M. Di Giacomo, G. Papeo, O. Caringo, C. Scolastico and L. Manzoni, Tetrahedron Lett., 1994, 35, 4031; (b) C. D. S. Brown, A. P. Dishington, O. Shishkin and N. S. Slmpkins, Synlett, 1995, 943; (c) C. J. Moody and C. L. Norton, Tetrahedron Lett., 1995, 36, 9051; (d) A. K. Mohanakrishnan and P. C. Srinivasan, Tetrahedron Lett., 1996, 37, 2659.
7. For recent examples, see (a) L. Colombo, M. Di Giacomo, G. Papeo, O. Caringo, C. Scolastico and L. Manzoni, Tetrahedron Lett., 1994, 35, 4031; (b) C. D. S. Brown, A. P. Dishington, O. Shishkin and N. S. Slmpkins, Synlett, 1995, 943; (c) C. J. Moody and C. L. Norton, Tetrahedron Lett., 1995, 36, 9051; (d) A. K. Mohanakrishnan and P. C. Srinivasan, Tetrahedron Lett., 1996, 37, 2659.
8. For recent examples, see (a) G. A. Molander and J. A. McKie, J. Org. Chem., 1994, 59, 3186; (b) K. Ghosh, A. K. Ghosh and U. R. Ghatak, J. Chem. Soc., Chem. Commun., 1994, 69; (c) F. O. H. Pirrung, H. Hiemstra, W. N. Speckamp, B. Kaptan and H. E. Schoemaker, Synthesis, 1995, 458; (d) G. A. Russell and C. Li, Tetrahedron Lett., 1996, 37, 2557; (e) E. Lee and C. H. Yoon, Tetrahedron Lett., 1996, 37, 5929.
9. For recent examples, see (a) G. A. Molander and J. A. McKie, J. Org. Chem., 1994, 59, 3186; (b) K. Ghosh, A. K. Ghosh and U. R. Ghatak, J. Chem. Soc., Chem. Commun., 1994, 69; (c) F. O. H. Pirrung, H. Hiemstra, W. N. Speckamp, B. Kaptan and H. E. Schoemaker, Synthesis, 1995, 458; (d) G. A. Russell and C. Li, Tetrahedron Lett., 1996, 37, 2557; (e) E. Lee and C. H. Yoon, Tetrahedron Lett., 1996, 37, 5929.
10. For recent examples, see (a) G. A. Molander and J. A. McKie, J. Org. Chem., 1994, 59, 3186; (b) K. Ghosh, A. K. Ghosh and U. R. Ghatak, J. Chem. Soc., Chem. Commun., 1994, 69; (c) F. O. H. Pirrung, H. Hiemstra, W. N. Speckamp, B. Kaptan and H. E. Schoemaker, Synthesis, 1995, 458; (d) G. A. Russell and C. Li, Tetrahedron Lett., 1996, 37, 2557; (e) E. Lee and C. H. Yoon, Tetrahedron Lett., 1996, 37, 5929.
11. For recent examples, see (a) G. A. Molander and J. A. McKie, J. Org. Chem., 1994, 59, 3186; (b) K. Ghosh, A. K. Ghosh and U. R. Ghatak, J. Chem. Soc., Chem. Commun., 1994, 69; (c) F. O. H. Pirrung, H. Hiemstra, W. N. Speckamp, B. Kaptan and H. E. Schoemaker, Synthesis, 1995, 458; (d) G. A. Russell and C. Li, Tetrahedron Lett., 1996, 37, 2557; (e) E. Lee and C. H. Yoon, Tetrahedron Lett., 1996, 37, 5929.
12. For recent examples, see (a) G. A. Molander and J. A. McKie, J. Org. Chem., 1994, 59, 3186; (b) K. Ghosh, A. K. Ghosh and U. R. Ghatak, J. Chem. Soc., Chem. Commun., 1994, 69; (c) F. O. H. Pirrung, H. Hiemstra, W. N. Speckamp, B. Kaptan and H. E. Schoemaker, Synthesis, 1995, 458; (d) G. A. Russell and C. Li, Tetrahedron Lett., 1996, 37, 2557; (e) E. Lee and C. H. Yoon, Tetrahedron Lett., 1996, 37, 5929.
13. K. Ghosh and U. R. Ghatak, Tetrahedron Lett., 1995, 36, 4897.
14. G. Pattenden, A. J. Smithies, D. Tapolczay and D. S. Walters, J. Chem. Soc., Perkin Trans. 1, 1996, 7.
15. (a) S. E. Gibson (née Thomas), N. Guillo, R. J. Middleton, A. Thuilliez and M. J. Tozer, J. Chem. Soc., Perkin Trans. 1, 1997, 447;
16. (b) S. E. Gibson (née Thomas) and R. J. Middleton, J. Chem. Soc., Chem. Commun., 1995, 1743.
17. See ref. 6(b) and references cited therein and S. Ma and E. Negishi, J. Am. Chem. Soc., 1995, 117, 6345.
18. S. E. Gibson (née Thomas), N. Guillo, S. B. Kalindjian and M. J. Tozer, unpublished results.
19. (a) A. Ali, G. B. Gill, G. Pattenden, G. A. Roan and T.-S. Kam, J. Chem. Soc., Perkin Trans. 1, 1996, 1081;
20. (b) J. H. Rigby and M. N. Qabas, J. Org. Chem., 1993, 58, 4473.
21. D. P. Curran and C.-T. Chang, J. Org. Chem., 1989, 54, 3140.