Diastereoselective photochemical synthesis of 3,3'-disubstituted indolines

Tetrahedron

Volumn 53, Issue 47, 1997, Pages 16083-16096

  Ibrahim Ouali, Malika ^a   Sinibaldi, Marie Ève ^a   Troin, Yves ^b   Guillaume, Dominique ^c   Gramain, Jean Claude ^a  

^a SEESIB   (France)

^b Lab Chim Heterocycles des Glucides   (France)

^c CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; IMIDE; INDOLINE DERIVATIVE; LACTAM DERIVATIVE; SPIROINDOLINE IMIDE DERIVATIVE; SPIROINDOLINE LACTAM DERIVATIVE; UNCLASSIFIED DRUG; VINDOROSINE;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; PHOTOCHEMISTRY; PRIORITY JOURNAL; STEREOCHEMISTRY;

ASPIDOSPERMA;

EID: 0030657808     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10028-X     Document Type: Article

References (31)

1. a) Rodriguez, J.G.; Benito, Y.; Temprano, F.J. Heterocyclic Chem. 1985, 22, 1207-1210.
2. b) Biswas, K.M.; Jackson, A.H.; Kobaisy, M.M.; Shannon, P.V.R. J. Chem. Soc. Perkin Trans 1 1994, 461-467.
3. c) Wilkins, D.J.; Jackson, A.H.; Shannon, P.V.R. J. Chem. Soc. Perkin Trans 1 1994, 299-307.
4. d) Williams, J. R.; Unger, L.R.; J. Chem. Soc., Chem. Commun. 1970, 1605-1606.
5. e) Freund, R.; Mahboobi, S.; Noack, K.; Schönholzer, P.; Bernauer, K. Helv. Chim. Acta 1990, 73, 439-454.
6. f) Grigg, R.; Fretwell, P.; Meerholtz, C.; Sridharan, V. Tetrahedron 1994, 50, 359-370.
7. g) Madin, A.; Overman, L.E. Tetrahedron Lett. 1992, 33, 4859-4862.
8. h) Rubiralta, M.; Diez, A.; Vila, C. Tetrahedron Lett. 1990, 31, 3347-3350.
9. i) Rubiralta, M.; Diez, A., Vila, C.; Troin, Y.; Feliz, M. J. Org. Chem. 1991, 56, 6292-6298.
10. j) Diez, A.; Vila, C.; Sinibaldi, M.-E., Troin, Y.; Rubiralta, M. Tetrahedron Lett. 1993, 34, 733-736.
11. k) Veenstra, S.J.; Fortgens, H.P.; Vijn, R.J.; De Jong, B.S.; Speckamp, W.N. Tetrahedron, 1987, 43, 1147-1156.
12. l) Speckamp, W.N. Recl. J. R. Neth. Chem. Soc. 1981, 100, 345-354.
13. m) Mittendorf, J.; Hiemstra, H.; Speckamp, W.N. Tetrahedron 1990,46, 4049-4062.
14. n) Vijn, R.J.; Speckamp, W.N.; De Jong, B.S.; Hiemstra, H. Angew. Chem. 1984, 96, 165-166.; Angew. Chem. Int. Ed. Engl. 1984, 23, 165-166.
15. n) Vijn, R.J.; Speckamp, W.N.; De Jong, B.S.; Hiemstra, H. Angew. Chem. 1984, 96, 165-166.; Angew. Chem. Int. Ed. Engl. 1984, 23, 165-166.
16. Ibrahim-Ouali, M.; Sinibaldi, M.-E.; Troin, Y.; Cuer, A.; Dauphin, G.; Gramain, J.-C. Heterocycles 1995, 41, 1939-1950.
17. Ibrahim-Ouali, M.; Sinibaldi, M.-E., Troin, Y., Gardette, D., Gramain, J.-C. Synth. Commun. 1997, 27, 1827-1848.
18. Ibrahim-Ouali, M.; Sinibaldi, M.-E.; Troin, Y.; Gramain, J.-C. Tetrahedron Lett. 1996, 37, 37-38.
19. a) Grellmann, K.H.; Sherman, G.M.; Linschitz, H. J. Am. Chem. Soc. 1963, 85, 1181-1182.
20. b) Chapmann, O.L.; Eian, G.L.; Bloom, A.; Clardy, J. J. Am. Chem. Soc. 1971, 93, 2918-2928.
21. c) Baron, U.; Bartelt, G.; Eychmüller, A.; Grellmann, K.H.; Schmitt, U.; Tauer, E.; Weller, H. J. Photochem. 1985, 28, 187-195.
22. d) Yamada, K.; Konakahara, T.; Iida, H. Bull. Chem. Soc. Jpn. 1973, 46, 2504-2511.
23. e) Gramain, J.-C.; Husson, H.-P.; Troin, Y. Tetrahedron Lett. 1985, 26, 2323-2326.
24. Riviere, M.; Paillous, N.; Lattes, A. Bull. Soc. Chim. Fr. 1974, 1911-1916.
25. Ninomiya, I.; Naito, Y. in Photochemical Synthesis, Katritzky, A.R.; Meth-Cohn, O. and Rees, C.W., Ed., Academic Press, London, 1989, p. 221.
26. 2 substituting C-3.
27. a) Santamaria, J.; Kaddachi, M.T.; Ferroud, C. Tetrahedron Lett. 1992, 33, 781-784 and references cited therein.
28. b) Théret-Bettiol, M.-H. Thesis, Paris XI University (Orsay), 1994.
29. Rousch, W.R. J. Am. Chem. Soc. 1980,102, 1390-1404.
30. Green, D.L.C.; Kiddle, J.J.; Thompson, C.M. Tetrahedron 1995, 51, 2865-2874.
31. Ram, S.; Spicer, L.D. Tetrahedron Lett. 1987, 28, 515-516.