Stereoselectivity of the reactions of N-phthaloyl iminium ions and ammo-substituted radicals derived from threonine

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2569-2572

  Renaud, Philippe ^a   Stojanovic, Aleksandar ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ISOINDOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029866254     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00387-5     Document Type: Article

References (25)

1. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995. Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296-304.
2. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995. Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296-304.
3. Bulliard, M.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1991, 74, 1600-1607.
4. Giese, B.; Damm, W.; Dickhaut, J.; Wetterich, F.; Sun, S.; Curran, D. P. Tetrahedron Lett. 1991, 32, 6097-6100.
5. Renaud, P.; Björup, P.; Carrupt, P.-A.; Schenk, K.; Schubert, S. Synlett 1992, 211-213. Schubert, S.; Renaud, P.; Carrupt, P. A.; Schenk, K. Helv. Chim. Acta. 1993, 76, 2473-2489. Renaud, P.; Bétrisey, I. Synth. Commun. 1995, 25, 3479-3491.
6. Renaud, P.; Björup, P.; Carrupt, P.-A.; Schenk, K.; Schubert, S. Synlett 1992, 211-213. Schubert, S.; Renaud, P.; Carrupt, P. A.; Schenk, K. Helv. Chim. Acta. 1993, 76, 2473-2489. Renaud, P.; Bétrisey, I. Synth. Commun. 1995, 25, 3479-3491.
7. Renaud, P.; Björup, P.; Carrupt, P.-A.; Schenk, K.; Schubert, S. Synlett 1992, 211-213. Schubert, S.; Renaud, P.; Carrupt, P. A.; Schenk, K. Helv. Chim. Acta. 1993, 76, 2473-2489. Renaud, P.; Bétrisey, I. Synth. Commun. 1995, 25, 3479-3491.
8. For a related work with amino-substituted radicals, see: Curran, D. P.; Thoma, G. J. Am. Chem. Soc. 1992, 114, 4436-4437. Curran, D. P.; Sun, S. N. Tetrahedron Lett .1993, 34, 6181-6184. Curran, D. P.; Eichenberger, E.; Collis, M.; Roepel, M. G.; Thoma, G. J. Am. Chem. Soc. 1994, 116, 4279-4288. Axon, J. R.; Beckwith, A. L. J. J. Chem. Soc., Chem. Commun. 1995, 549-550.
9. For a related work with amino-substituted radicals, see: Curran, D. P.; Thoma, G. J. Am. Chem. Soc. 1992, 114, 4436-4437. Curran, D. P.; Sun, S. N. Tetrahedron Lett .1993, 34, 6181-6184. Curran, D. P.; Eichenberger, E.; Collis, M.; Roepel, M. G.; Thoma, G. J. Am. Chem. Soc. 1994, 116, 4279-4288. Axon, J. R.; Beckwith, A. L. J. J. Chem. Soc., Chem. Commun. 1995, 549-550.
10. For a related work with amino-substituted radicals, see: Curran, D. P.; Thoma, G. J. Am. Chem. Soc. 1992, 114, 4436-4437. Curran, D. P.; Sun, S. N. Tetrahedron Lett .1993, 34, 6181-6184. Curran, D. P.; Eichenberger, E.; Collis, M.; Roepel, M. G.; Thoma, G. J. Am. Chem. Soc. 1994, 116, 4279-4288. Axon, J. R.; Beckwith, A. L. J. J. Chem. Soc., Chem. Commun. 1995, 549-550.
11. For a related work with amino-substituted radicals, see: Curran, D. P.; Thoma, G. J. Am. Chem. Soc. 1992, 114, 4436-4437. Curran, D. P.; Sun, S. N. Tetrahedron Lett .1993, 34, 6181-6184. Curran, D. P.; Eichenberger, E.; Collis, M.; Roepel, M. G.; Thoma, G. J. Am. Chem. Soc. 1994, 116, 4279-4288. Axon, J. R.; Beckwith, A. L. J. J. Chem. Soc., Chem. Commun. 1995, 549-550.
12. Hutchins, R. O.; Su, W.-Y.; Sivakumar, R.; Cistone, F.; Stercho, Y. P. J. Org. Chem. 1983,48, 3412-3422.
13. For a related work on phthalimido substituted radicals, see: (a) Damm, W.; Hoffmann, U.; Macko, L.; Neuburger, M.; Zehnder, M.; Giese, B. Tetrahedron 1994, 50, 7029-7048. For one related example, see:
14. (b) Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116-118.
15. A slightly higher selectivity (synlanti 9:1) was observed by Giese using a TBDMS instead of a TIPS as protective group: see ref. 7b.
16. Barton, D. H. R.; Hervé, Y.; Potier, P.; Thierry, J. Tetrahedron 1987, 43, 4297-4308.
17. 3): 7.86-7.69 (m, 4H); 4.32 (quint, 1H, J = 6.1); 3.74 (d, 1H, J = 6.1, major isomer); 3.60 ( d, 1H, J = 7.0, minor isomer); 1.20 (d, 1H, J = 6.1); 1.05 (s, 21H).
18. 1H-NMR spectra and proved by chemical correlation. Further details will be published in a forthcoming full paper.
19. 13C-NMR spectra with the data reported in reference 7a.
20. For radical addition to dehydroalanine derivatives, see: Beckwith, A. L. J.; Chai, C. L. L. J. Chem. Soc., Chem. Commun., 1990, 1087-1088. Chai, C. L. L.; King, A. R. Tetrahedron 1995, 36, 4295-4298. Crich, D.; Davies, J. W. Tetrahedron 1989, 45, 5641-5654. Gasanov, R. G.; Il'inskaya, L. V.; Misharin, M. A.; Maleev, V. I.; Raevski, N. I.; Ikonnikov, N. S.; Orlova, S. A.; Kuzmina, N. A.; Belokon, Y. N. J. Chem. Soc. Perkin Trans. 1 1994, 3343-3348. Kessler, V. H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem. Int. Ed. Engl. 1992, 31, 874-877.
21. For radical addition to dehydroalanine derivatives, see: Beckwith, A. L. J.; Chai, C. L. L. J. Chem. Soc., Chem. Commun., 1990, 1087-1088. Chai, C. L. L.; King, A. R. Tetrahedron 1995, 36, 4295-4298. Crich, D.; Davies, J. W. Tetrahedron 1989, 45, 5641-5654. Gasanov, R. G.; Il'inskaya, L. V.; Misharin, M. A.; Maleev, V. I.; Raevski, N. I.; Ikonnikov, N. S.; Orlova, S. A.; Kuzmina, N. A.; Belokon, Y. N. J. Chem. Soc. Perkin Trans. 1 1994, 3343-3348. Kessler, V. H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem. Int. Ed. Engl. 1992, 31, 874-877.
22. For radical addition to dehydroalanine derivatives, see: Beckwith, A. L. J.; Chai, C. L. L. J. Chem. Soc., Chem. Commun., 1990, 1087-1088. Chai, C. L. L.; King, A. R. Tetrahedron 1995, 36, 4295-4298. Crich, D.; Davies, J. W. Tetrahedron 1989, 45, 5641-5654. Gasanov, R. G.; Il'inskaya, L. V.; Misharin, M. A.; Maleev, V. I.; Raevski, N. I.; Ikonnikov, N. S.; Orlova, S. A.; Kuzmina, N. A.; Belokon, Y. N. J. Chem. Soc. Perkin Trans. 1 1994, 3343-3348. Kessler, V. H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem. Int. Ed. Engl. 1992, 31, 874-877.
23. For radical addition to dehydroalanine derivatives, see: Beckwith, A. L. J.; Chai, C. L. L. J. Chem. Soc., Chem. Commun., 1990, 1087-1088. Chai, C. L. L.; King, A. R. Tetrahedron 1995, 36, 4295-4298. Crich, D.; Davies, J. W. Tetrahedron 1989, 45, 5641-5654. Gasanov, R. G.; Il'inskaya, L. V.; Misharin, M. A.; Maleev, V. I.; Raevski, N. I.; Ikonnikov, N. S.; Orlova, S. A.; Kuzmina, N. A.; Belokon, Y. N. J. Chem. Soc. Perkin Trans. 1 1994, 3343-3348. Kessler, V. H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem. Int. Ed. Engl. 1992, 31, 874-877.
24. For radical addition to dehydroalanine derivatives, see: Beckwith, A. L. J.; Chai, C. L. L. J. Chem. Soc., Chem. Commun., 1990, 1087-1088. Chai, C. L. L.; King, A. R. Tetrahedron 1995, 36, 4295-4298. Crich, D.; Davies, J. W. Tetrahedron 1989, 45, 5641-5654. Gasanov, R. G.; Il'inskaya, L. V.; Misharin, M. A.; Maleev, V. I.; Raevski, N. I.; Ikonnikov, N. S.; Orlova, S. A.; Kuzmina, N. A.; Belokon, Y. N. J. Chem. Soc. Perkin Trans. 1 1994, 3343-3348. Kessler, V. H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem. Int. Ed. Engl. 1992, 31, 874-877.
25. 3, major isomer): 7.82-7.69 (m, 4H); 5.67 (m, 1H); 4.96 (dd, 1H, J = 17.1, 1.3); 4.87 (dm, 1H, J = 10.3); 4.58 (dq, 1H, J = 9.0, 6.1); 4.13 (td, 1H, J = 9.4, 5.9); 2.85 (m, 2H); 1.13 (d, 3H, J = 6.1), 1.08 (m, 21H).