Additions of lithiated alkoxyallenes to phthalimide: A new synthesis of pyrroloisoindolones and an unusual olefination reaction

Synthesis

Volumn , Issue 8, 2006, Pages 1351-1359

  Kaden, Silvia ^a   Reissig, Hans Ulrich ^a   Brüdgam, Irene ^a   Hartl, Hans ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Allenes; Gold catalysis; Imide; Lithium; Pyrroloisoindolones

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CHLORINE; DERIVATIVES; GOLD; HYDROXYLATION; LITHIUM; OXYGEN; SULFURIC ACID; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

ALLENES; GOLD CATALYSIS; IMIDE; PYRROLOISOINDOLONES;

ORGANIC COMPOUNDS;

1 (2 TRIMETHYLSILYL)ETHOXY 5H PYRROLO[2,1 A]ISOINDOL 5 ONE; 1 (BENZYLOXY) 5H PYRROLO[2,1 A]ISOINDOL 5 ONE; 1 METHOXY 5H PYRROLO[2,1 A]ISOINDOL 5 ONE; 3 (1 BENZYLOXY 2 OXOPROPYLIDENE) 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 (1 METHOXY 2 OXOPROPYLIDENE) 2 METHYL 2,3 DIHYDROISOINDOL 1 ONE; 3 (1 METHOXY 2 OXOPROPYLIDENE) 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 (1 METHOXYPROPA 1,2 DIENYL) 3 (TRIMETHYLSILOXY) 2,3 DIHYDROISOINDOL 1 ONE; 3 (2 CHLORO 1 METHOXYPROP 2 ENYLIDENE) 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 [1 (2 TRIMETHYLSILYLETHOXY)PROPA 1,2 DIENYL] 3 HYDROXYISOINDOLIN 1 ONE; 3 [1 (BENZYLOXY)PROPA 1,2 DIENYL] 3 (TRIMETHYLSILYLOXY)ISOINDOLIN 1 ONE; 3 [1 (BENZYLOXY)PROPA 1,2 DIENYL] 3 HYDROXYISOINDOLIN 1 ONE; 3 [1 [(2 TRIMETHYLSILYL)ETHOXY]PROPA 1,2 DIENYL] 3 (TRIMETHYLSILOXY)ISOINDOLIN 1 ONE; 3 [2 OXO 1 [2 (2 TRIMETHYLSILYL)ETHOXY]PROPYLIDENE] 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 HYDROXY 3 (1 METHOXYPROPA 1,2 DIENYL)ISOINDOLIN 1 ONE; 4' (2 TRIMETHYLSILYL)ETHOXY 3A,7A BENZO 1' OXA 2 AZASPIROL[4,4]NON 3' EN 1 ONE; 4' BENZYLOXY 3A,7A BENZO 1' OXA 2 AZASPIRO[4,4]NON 3' EN 1 ONE; 4' METHOXY 3A,7A BENZO 1' OXA 2 AZASPIROL[4,4]NON 3' EN 1 ONE; ALKOXYALLENE DERIVATIVE; ALLENE DERIVATIVE; CHLORINE; FURAN DERIVATIVE; GOLD; HYDROCHLORIC ACID; ISOINDOLE DERIVATIVE; OXYGEN; PHTHALIMIDE; PYRROLOISOINDOLONE DERIVATIVE; SULFURIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; CYCLIZATION; HECK REACTION; OLEFINATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 33646252965     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926399     Document Type: Article

References (41)

1. (a) Hoff, S.; Brandsma, L.; Arens, J. F. Recl. Trav. Chim. Pays-Bas 1969, 88, 609.
2. (b) Hormuth, S.; Reissig, H.-U. Synlett 1991, 179.
3. (c) Hormuth, S.; Reissig, H.-U. J. Org. Chem. 1994, 59, 67.
4. (d) Hormuth, S.; Schade, W.; Reissig, H.-U. Liebigs Ann. Chem. 1996, 2001.
5. Okala Amombo, G. M.; Hausherr, A.; Reissig, H.-U. Synlett 1999, 1871.
6. (a) Schade, W.; Reissig, H.-U. Synlett 1999, 632.
7. (b) Helms, M.; Schade, W.; Pulz, R.; Watanabe, T.; Al-Harrasi, A.; Fisera, L.; Hlobilova, I.; Zahn, G.; Reissig, H.-U. Eur. J. Org. Chem. 2005, 1003.
8. (a) Reissig, H.-U.; Hormuth, S.; Schade, W.; Okala Amombo, G. M.; Watanabe, T.; Pulz, R.; Hausherr, A.; Zimmer, R. Lectures in Heterocyclic Chemistry Vol. XVI, In J. Heterocycl. Chem. 2000, 37, 597.
9. (b) Reissig, H.-U.; Schade, W.; Okala Amombo, G. M.; Pulz, R.; Hausherr, A. Pure Appl. Chem. 2002, 74, 175.
10. (a) Zimmer, R. Synthesis 1993, 165.
11. (b) Zimmer, R.; Reissig, H.-U. Donor-Substituted Allenes, In Modern Allene Chemistry; Krause, N.; Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004, Chap. 8. 425.
12. (a) Hausherr, A. Ph.D. Dissertation: Freie Universität Berlin: Germany, 2001.
13. (b) Flögel, O.; Okala Amombo, G. M.; Reissig, H.-U.; Zahn, G.; Brüdgam, I.; Hartl, H. Chem. Eur. J. 2003, 9, 1405.
14. (c) Kaden, S.; Brockmann, M.; Reissig, H.-U. Helv. Chim. Acta 2005, 88, 1826.
15. Al-Harrasi, A.; Reissig, H.-U. Angew. Chem. Int. Ed. 2005, 44, 6227;
16. Angew. Chem. 2005, 117, 6383.
17. Honma, T.; Hayashi, K.; Aoyama, T.; Hashimoto, N.; Machida, T.; Fukasawa, K.; Iwama, T.; Ikeura, C.; Suzuki-Takahashi, I.; Iwasawa, Y.; Hayama, T.; Nishimura, S.; Morishima, H. J. Med. Chem. 2001, 44, 4615.
18. Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1990, 46, 4003.
19. (a) Itahara, T. J. Chem. Soc., Chem. Commun. 1981, 254.
20. For photoinduced cyclizations, see also: (b) Schmickler, H.; Bartoschek, A.; Kramer, W.; Griesbeck, A. G. Org. Lett. 2001, 3, 537.
21. Wang, E.-C.; Chen, H.-F.; Feng, P.-K.; Lin, Y.-L.; Hsu, M.-K. Tetrahedron Lett. 2002, 43, 9163.
22. (a) Claesson, A.; Sahlberg, C.; Luthman, K. Acta Chem. Scand. Ser. B 1979, 33, 309.
23. (b) Robinson, E. D.; Marshall, J. A. J. Org. Chem. 1990, 55, 3450.
24. (c) Bartley, G. S.; Marshall, J. A. J. Org. Chem. 1994, 59, 7169.
25. Okala Amombo, G. M. Ph.D. Dissertation; Technische Universität Dresden: Germany, 2000.
26. (a) Frost, T. M.; Choi, J.-H.; Schwarz, L.; Hashmi, A. S. K. Angew. Chem. Int. Ed. 2000, 39, 2285;
27. Angew. Chem. 2000, 112, 2382.
28. (b) Gagosz, F. Org. Lett. 2005, 7, 4129.
29. For reviews see: (c) Dyker, G. Angew. Chem. Int. Ed. 2000, 39, 4237;
30. Angew. Chem. 2000, 112, 4407.
31. (d) Hashmi, A. S. K. Gold Bull. 2003, 36, 3.
32. (e) Echavarren, A. M.; Nevado, C. Chem. Soc. Rev. 2004, 33, 431.
33. (a) Hoffmann-Röder, A.; Krause, N. Org. Lett. 2001, 3, 2537.
34. (b) Morita, N.; Krause, N. Org. Lett. 2004, 6, 4121.
35. (c) See also: Lee, P. H.; Kim, H.; Lee, K.; Kim, M.; Noh, K.; Kim, H.; Seomon, D. Angew. Chem. Int. Ed. 2005, 44, 1840;
36. Angew. Chem. 2005, 117, 1874.
37. Flögel, O.; Dash, J.; Brüdgam, I.; Hartl, H.; Reissig, H.-U. Chem. Eur. J. 2004, 10, 4283.
38. (a) Reppe, W. Liebigs Ann. Chem. 1955, 596, 1.
39. (b) Weiberth, F. J.; Hall, S. S. J. Org. Chem. 1985, 50, 5308.
40. ( 18) Sheldrick, G. M. SHELX97 (includes SHELXS97, SHELXL97, and CIFTAB) Programs for Crystal Structure Analysis (Release 97-2); Universität Göttingen: Germany, 1998.
41. Crystallographic data for 15a can be obtained from Cambridge Crystallographic Data Centre, CCDC reference number: 286363.