A stereoselective synthesis of (Z)-3-aryl and alkylmethylidene-1H- isoindolin-1-ones

Synthesis

Volumn , Issue 8, 2006, Pages 1333-1338

  Lamblin, Marc ^a   Couture, Axel ^a   Deniau, Eric ^a   Grandclaudon, Pierre ^a  

^a UNIV LILLE   (France)

Author keywords

Carbanions; Cyclizations; Mitsonobu reaction; Olefination; Stereoselectivity

Indexed keywords

ALDEHYDES; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

CARBANIONS; CYCLIZATIONS; MITSONOBU REACTION; OLEFINATION; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

ALDEHYDE DERIVATIVE; CARBAMIC ACID DERIVATIVE; ISOINDOLE DERIVATIVE; METHYLIDENE 1H ISOINDOLIN 1 ONE DERIVATIVE; N (2 IODOARYLMETHYL)DICARBAMATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 33646230066     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926413     Document Type: Article

References (44)

1. Kato, Y.; Takemoto, M.; Achiwa, K. Chem. Pharm. Bull. 1993, 41, 2003.
2. Pigeon, P.; Decroix, B. Tetrahedron Lett. 1996, 37, 7707.
3. Achimani, K.; Ashizawa, N.; Kobayashi, F. Jpn Patent JP 03133955, 1991; Chem. Abstr. 1991, 115, 255977.
4. Laboratori Baldacci S.p.A.; Jpn Patent JP 5946268, 1984; Chem. Abstr. 1984, 101, 54922.
5. Rys, V.; Couture, A.; Deniau, E.; Grandclaudon, P. Tetrahedron 2003, 59, 6615.
6. Couture, A.; Deniau, E.; Grandclaudon, P.; Hoarau, C. Tetrahedron 2000, 56, 1491.
7. Castedo, L.; Guitián, E.; Saá, J. M.; Suau, R. Heterocycles 1982, 19, 279.
8. Moreau, A.; Couture, A.; Deniau, E.; Grandclaudon, P. J. Org. Chem. 2004, 69, 4527.
9. Uozumi, Y.; Mori, E.; Mori, M.; Shibasaki, M. J. Organomet. Chem. 1990, 399, 93.
10. (a) Li, Z.; Zhang, Y. Tetrahedron Lett. 2001, 42, 8507.
11. (b) Sánchez-Sánchez, C.; Pérez-Inestrosa, E.; García-Segura, R.; Suau, R. Tetrahedron 2002, 58, 7267.
12. (c) Kato, Y.; Takemoto, M.; Achiwa, K. Chem. Pharm. Bull. 1999, 47, 529.
13. (d) Kato, Y.; Ebiike, H.; Achiwa, N.; Kurihara, T.; Kobakashi, F. Chem. Pharm. Bull. 1990, 38, 2060.
14. (e) Hitchings, G. J.; Vernon, J. M. J. Chem. Soc., Perkin Trans. 1 1990, 1757.
15. (a) Griesbeck, A. G.; Warzecha, K.-D.; Neudoerfl, J. M.; Goerner, H. Synlett 2004, 2347.
16. (b) Griesbeck, A. G.; Kramer, W.; Oelgemoller, M. Synlett 1999, 1169.
17. Flitsch, W.; Howard, P. Tetrahedron Lett. 1969, 1161.
18. (a) Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 1432.
19. (b) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
20. (c) Kundu, N. G.; Khan, M. W. Tetrahedron 2000, 56, 4777.
21. (d) Wu, M.-J.; Chang, L.-J.; Wei, L.-M.; Lin, C.-F. Tetrahedron 1999, 55, 13193.
22. (e) Khan, M. W.; Kundu, N. G. Synlett 1997, 1435.
23. (f) Vasilevskii, S. F.; Shvartsberg, M. S. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 9, 1901.
24. Lu, W.-D.; Lin, C.-F.; Wang, C.-J.; Wang, S.-J.; Wu, M.-J. Tetrahedron 2002, 58, 7315.
25. Couty, S.; Liegault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511.
26. Uozumi, Y.; Kawasaki, N.; Mori, E.; Mori, M.; Shibasaki, M. J. Am. Chem. Soc. 1989, 111, 3725.
27. ( 17) Hendi, M. S.; Natalie, K. J. Jr.; Hendi, S. B.; Campbell, J. A.; Greenwood, T. D.; Wolfe, J. F. Tetrahedron Lett. 1989, 30, 275.
28. Gramain, J.-C.; Mavel, S.; Troin, Y.; Vallée-Goyet, D. Tetrahedron 1991, 47, 7287.
29. Couture, A.; Deniau, E.; Ionescu, D.; Grandclaudon, P. Tetrahedron Lett. 1998, 39, 2319.
30. Rico, R.; Bermejo, F. Tetrahedron Lett. 1996, 37, 5809.
31. Li, W.-R.; Lin, S. T.; Hsu, N.-M.; Chern, M.-S. J. Org. Chem. 2002, 67, 4702.
32. Couture, A.; Deniau, E.; Grandclaudon, P.; Hoarau, C.; Rys, V. Tetrahedron Lett. 2002, 43, 2207.
33. (a) Sotomayor, N.; Lete, E. Curr. Org. Chem. 2003, 7, 275.
34. (b) Najera, C.; Sansano, J. M.; Yus, M. Tetrahedron 2003, 59, 9255.
35. (c) Parham, W. E.; Bradsher, C. K. Acc. Chem. Res. 1982, 15, 300.
36. (d) Moreau, A.; Couture, A.; Deniau, E.; Grandclaudon, P.; Lebrun, S. Org. Biomol. Chem. 2005, 3, 3437.
37. (a) Thurber, T. C.; Townsend, L. B. J. Heterocycl. Chem. 1977, 14, 647.
38. (b) Shi, S.; Katz, T. J.; Yang, B. V.; Liu, L. J. Org. Chem. 1995, 60, 1285.
39. Takeuchi, Y.; Nabetani, M.; Takagi, K.; Hagi, T.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1991, 49.
40. Ruiz, J.; Sotomayor, N.; Lete, E. Org. Lett. 2003, 5, 1115.
41. Ziegler, F. E.; Schwartz, J. A. J. Org. Chem. 1978, 43, 985.
42. Guillaumel, J.; Boccara, N.; Demerseman, P.; Royer, R.; Bideau, J.-P.; Cotrait, M.; Platzer, N. J. Heterocycl. Chem. 1990, 27, 605.
43. Sekiya, M.; Terao, Y. Yakugaku Zasshi 1968, 88, 1085;
44. Chem. Abstr. 1969, 70, 3488.