Synthesis of s-indacene derivatives by double Robinson-type cyclopentene annulation

Synthesis

Volumn , Issue 19, 2007, Pages 3061-3067

  Zhang, Yawei ^a   Christoffers, Jens ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

Aldol reaction; Annulation; Conjugate addition; Cyclopentene; Indacene

Indexed keywords

ANNULATION; CONJUGATE ADDITION; CYCLOPENTENE; INDACENE;

ADDITION REACTIONS; DERIVATIVES; REACTION KINETICS;

ALCOHOLS;

2,5 DIOXOCYCLOHEXANE 1,4 DICARBOXYLATE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIALLYL 2,5 DIHYDROXYCYCLOHEXA 1,4 DIENE 1,4 DICARBOXYLATE; DIALLYL CIS 1,5 DIMETHYL 4,8 DIOXO 2,3,3A,4,6,7,7A,8 OCTAHYDRO S INDACENE 3A,7A DICARBOXYLATE; DIALLYL CIS 2,5 DIOXO 1,4 BIS(3 OXOBUTYL)CYCLOHEXANE 1,4 DICARBOXYLATE; DIBENZYL 2,5 DIHYDROXYCYCLOHEXA 1,4 DIENE 1,4 DICARBOXYLATE; DIBENZYL CIS 1,5 DIMETHYL 4,8 DIOXO 2,3,3A,4,6,7,7A,8 OCTAHYDRO S INDACENE 3A,7A DICARBOXYLATE; DIBENZYL CIS 2,5 DIOXO 1,5 BIS(3 OXOBUTYL)CYCLOHEXANE 1,4 DICARBOXYLATE; DIETHYL CIS 1,5 DIMETHYL 4,8 DIOXO 2,3,3A,4,6,7,7A,8 OCTAHYDRO S INDACENE 3A,7A DICARBOXYLATE; DIETHYL CIS 2,5 DIOXO 1,4 BIS(3 OXOBUTYL)CYCLOHEXANE 1,4 DICARBOXYLATE; DIOCTYL 2,5 DIHYDROXYCYCLOHEXA 1,4 DIENE 1,4 DICARBOXYLATE; DIOCTYL CIS 1,5 DIMETHYL 4,8 DIOXO 2,3,3A,4,6,7,7A,8 OCTAHYDRO S INDACENE 3A,7A DICARBOXYLATE; DIOCTYL CIS 2,5 DIOXO 1,4 BIS(3 OXOBUTYL)CYCLOHEXANE 1,4 DICARBOXYLATE; INDACENE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DECARBOXYLATION; DIASTEREOISOMER; MICHAEL ADDITION; SYNTHESIS;

EID: 35348954896     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983901     Document Type: Article

References (49)

1. Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, 2004.
2. Christoffers, J. In Encyclopedia of Catalysis, Vol. 5; Horvath, I., Ed.; Wiley: New York, 2003, 99.
3. (a) Rapson, W. S.; Robinson, R. J. Chem. Soc. 1935, 1285.
4. Reviews: (b) Gawley, R. E. Synthesis 1976, 777.
5. (c) Jung, M. E. Tetrahedron 1976, 32, 3.
6. Recent examples: (a) Kraft, P.; Weymuth, C.; Nussbaumer, C. Eur. J. Org. Chem. 2006, 1403.
7. (b) Röttger, S.; Waldmann, H. Eur. J. Org. Chem. 2006, 2093.
8. (c) Payette, J. N.; Honda, T.; Yoshizawa, H.; Favaloro, F. G.; Gribble, G. W. J. Org. Chem. 2006, 71, 416.
9. (d) Gan, Y.; Spencer, T. A. J. Org. Chem. 2006, 71, 5870.
10. (a) Kreidler, B.; Baro, A.; Christoffers, J. Eur. J. Org. Chem. 2005, 5339.
11. (b) Kreidler, B.; Baro, A.; Frey, W.; Christoffers, J. Chem. Eur. J. 2005, 11, 2660.
12. (c) Kreidler, B.; Baro, A.; Christoffers, J. Synlett 2005, 465. Review:
13. (d) Christoffers, J. Chem. Eur. J. 2003, 9, 4862.
14. (a) Christoffers, J. Synlett 2006, 318.
15. (b) Christoffers, J.; Scharl, H.; Frey, W.; Baro, A. Eur. J. Org. Chem. 2004, 2701.
16. (c) Christoffers, J.; Scharl, H.; Frey, W.; Baro, A. Org. Lett. 2004, 6, 1171.
17. (d) Christoffers, J.; Scharl, H. Eur. J. Org. Chem. 2002, 1505.
18. Christoffers, J.; Zhang, Y.; Frey, W.; Fischer, P. Synlett 2006, 624.
19. Buchanan, G. L.; Kennedy, W. B.; Lawson, A. M. J. Chem. Soc., Perkin Trans. 1 1977, 32.
20. (a) García Cuesta, I.; Coriani, S.; Lazzeretti, P.; Sánchez de Merás, A. M. J. ChemPhysChem 2006, 7, 240.
21. (b) Güell, M.; Matito, E.; Luis, J. M.; Poater, J.; Sola, M. J. Phys. Chem. A 2006, 110, 11569.
22. (a) Dahrouch, M.; Burgos, F.; Castel, A.; Chavez, I.; Gornitzka, H.; Manriquez, J. M.; Riviere, P.; Riviere-Baudet, M.; Alvarez, J.; Onyszchuk, M. Appl. Organomet. Chem. 2007, 21, 31.
23. (b) Lian, J.-J.; Lin, C.-C.; Chang, H.-K.; Chen, P.-C.; Liu, R.-S. J. Am. Chem. Soc. 2006, 128, 9661.
24. (c) Dahrouch, M. R.; Jara, P.; Mendez, L.; Portilla, Y.; Abril, D.; Alfonso, G.; Chavez, I.; Manriquez, J. M. Organometallics 2001, 20, 5591.
25. (d) Hafner, K.; Stowasser, B.; Krimmer, H.-P.; Fischer, S.; Böhm, M. C.; Lindner, H. J. Angew. Chem., Int. Ed. Engl. 1986, 25, 630;
26. Angew. Chem. 1986, 98, 646.
27. (e) Birladeanu, L.; Chamot, E.; Fristad, W. E.; Paquette, L. A.; Winstein, S. J. Org. Chem. 1977, 42, 3260.
28. (f) LeGoff, E.; LaCount, R. B. Tetrahedron Lett. 1964, 5, 1161.
29. (a) Hudlicky, T.; Fleming, A.; Radesca, L. J. Am. Chem. Soc. 1989, 111, 6691.
30. (b) Woodward, R. B.; Hoye, T. R. J. Am. Chem. Soc. 1977, 99, 8007.
31. (a) Esponda, E.; Adams, C.; Burgos, F.; Chavez, I.; Manriquez, J. M.; Delpech, F.; Castel, A.; Gornitzka, H.; Riviere-Baudet, M.; Riviere, P. J. Organomet. Chem. 2006, 691, 3011.
32. (b) Roussel, P.; Cary, D. R.; Barlow, S.; Green, J. C.; Varret, F.; O'Hare, D. Organometallics 2000, 19, 1071.
33. (c) Bell, W. L.; Curtis, C. J.; Eigenbrot, C. W.; Pierpont, C. P.; Robbins, J. L.; Smart, J. C. Organometallics 1987, 6, 266.
34. (a) Chen, H. Z.; Jin, Y. D.; Xu, R. S.; Peng, B. X.; Desseyn, H.; Janssens, J.; Heremans, P.; Borghs, G.; Geise, H. J. Synth. Met. 2003, 139, 529.
35. (b) Halterman, R. L.; Jan, S.-T.; Abdulwali, A. H.; Standlee, D. J. Tetrahedron 1997, 53, 11277.
36. (a) Bauer, M.; Kauf, T.; Christoffers, J.; Bertagnolli, H. Phys. Chem. Chem. Phys. 2005, 7, 2664.
37. (b) Pelzer, S.; Kauf, T.; van Wüllen, C.; Christoffers, J. J. Organomet. Chem. 2003, 684, 308.
38. Review: (c) Christoffers, J. Synlett 2001, 723.
39. Christoffers, J.; Oertling, H.; Önal, N. J. Prakt. Chem. 2000, 342, 546.
40. Christoffers, J.; Schuster, K. Chirality 2003, 15, 777.
41. Christoffers, J.; Mann, A. Eur. J. Org. Chem. 2000, 1977.
42. Tsuji, J.; Nisar, M.; Shimizu, I. J. Org. Chem. 1985, 50, 3416.
43. Liebermann, H. Justus Liebigs Ann. Chem. 1914, 404, 272.
44. Moore, J. A. Org. Prep. Proced. Int. 1972, 4, 31.
45. (a) Kan, R. O. J. Am. Chem. Soc. 1964, 86, 5180.
46. (b) Bischoff, C. A.; von Hedenström, A. Chem. Ber. 1902, 35, 4073.
47. Sinnreich, J.; Batzer, H. Helv. Chim. Acta 1979, 62, 1682.
48. Akutsu, M. JP 61011290,1986; Chem. Abstr. 1986, 105, 33055.
49. Takahashi, K.; Shibagaki, M.; Matsushita, H. Bull. Chem. Soc. Jpn. 1989, 62, 2353.