A two-step reaction sequence for the syntheses of tetrahydronaphthalenes

Organic Letters

Volumn 7, Issue 2, 2005, Pages 251-253

  Hilt, Gerhard ^a   Lüers, Steffen ^a   Smolko, Konstantin I ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; BORON DERIVATIVE; COBALT DERIVATIVE; NAPHTHALENE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; SYNTHESIS;

EID: 13444311858     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0477879     Document Type: Article

References (28)

1. (a) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101.
2. (b) Ugi, I.; A. Dömling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647.
3. (c) Weber, L.; Illgen, K.; Almstetter, M. Synlett 1999, 366.
4. Hilt, G.; Smolko, K. I. Angew. Chem. 2003, 115, 2901; Angew. Chem., Int. Ed. 2003, 42, 2795.
5. Hilt, G.; Smolko, K. I. Angew. Chem. 2003, 115, 2901; Angew. Chem., Int. Ed. 2003, 42, 2795.
6. (a) Toure, B. B.; Hall, D. G. Angew. Chem. 2004, 116, 2035; Angew. Chem., Int. Ed. 2004, 43, 2001.
7. (a) Toure, B. B.; Hall, D. G. Angew. Chem. 2004, 116, 2035; Angew. Chem., Int. Ed. 2004, 43, 2001.
8. (b) Deligny, M.; Carreaux, F.; Toupet, L.; Carboni, B. Adv. Synth. Catal. 2003, 345, 1215.
9. (c) Gao, X.; Hall, D. G. Tetrahedron Lett. 2003, 44, 2231.
10. (d) Toure, B. B.; Hoveyda, H. R.; Tailor, J.; Ulaczyk-Lesanko, A.; Hall, D. G. Chem. Eur. J. 2003, 9, 466.
11. (e) Deligny, M.; Carreaux, F.; Carboni, B.; Toupet, L.; Dujardin, G. Chem. Commun. 2003, 276.
12. (f) Lallemand, J.-Y.; Six, Y.; Ricard, L. Eur. J. Org. Chem. 2002, 503.
13. (g) Vaultier, M.; Truchet, F.; Carboni, B.; Hoffmann, R. W.; Denne, I. Tetrahedron Lett. 1987, 28, 4169.
14. For the Diels-Alder reactions with highly substituted 1,3-dienes see: (a) Schmittel, M.; Von Seggern, H. J. Am. Chem. Soc. 1993, 115, 2165. (b) Wehbe, M.; Lepage, L.; Lepage, Y.; Platzer, N. Bull. Soc. Chim. Fr. 1987, 309. (c) Majo, V. J.; Suzuki, S.; Toyota, M.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 2000, 3375. (d) Phansavath, P.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1998, 39, 1561. (e) Tjepkema, M. W.; Wilson, P. D.; Audrain, H.; Fallis, A. G. Can. J. Chem. 1997, 75, 1215. (f) Dai, W.-M.; Lau, C. W.; Chung, S. H.; Wu, Y. D. J. Org. Chem. 1995, 60, 8128. (g) Graziano, M.; Iesce, M. R.; Cermola, F. Synthesis 1994, 149. (h) Nicolaou, K. C.; Hwang, C. K.; Sorensen, E. J.; Clairborne, C. F. J. Chem. Soc., Chem. Commun. 1992, 1117. (i) Bonnert, R. V.; Jenkins, P. R. Tetrahedron Lett. 1987, 28, 697. (j) Erman, W. F.; Stone, L. C. J. Am. Chem. Soc. 1971, 93, 2821.
15. For the Diels-Alder reactions with highly substituted 1,3-dienes see: (a) Schmittel, M.; Von Seggern, H. J. Am. Chem. Soc. 1993, 115, 2165. (b) Wehbe, M.; Lepage, L.; Lepage, Y.; Platzer, N. Bull. Soc. Chim. Fr. 1987, 309. (c) Majo, V. J.; Suzuki, S.; Toyota, M.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 2000, 3375. (d) Phansavath, P.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1998, 39, 1561. (e) Tjepkema, M. W.; Wilson, P. D.; Audrain, H.; Fallis, A. G. Can. J. Chem. 1997, 75, 1215. (f) Dai, W.-M.; Lau, C. W.; Chung, S. H.; Wu, Y. D. J. Org. Chem. 1995, 60, 8128. (g) Graziano, M.; Iesce, M. R.; Cermola, F. Synthesis 1994, 149. (h) Nicolaou, K. C.; Hwang, C. K.; Sorensen, E. J.; Clairborne, C. F. J. Chem. Soc., Chem. Commun. 1992, 1117. (i) Bonnert, R. V.; Jenkins, P. R. Tetrahedron Lett. 1987, 28, 697. (j) Erman, W. F.; Stone, L. C. J. Am. Chem. Soc. 1971, 93, 2821.
16. For the Diels-Alder reactions with highly substituted 1,3-dienes see: (a) Schmittel, M.; Von Seggern, H. J. Am. Chem. Soc. 1993, 115, 2165. (b) Wehbe, M.; Lepage, L.; Lepage, Y.; Platzer, N. Bull. Soc. Chim. Fr. 1987, 309. (c) Majo, V. J.; Suzuki, S.; Toyota, M.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 2000, 3375. (d) Phansavath, P.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1998, 39, 1561. (e) Tjepkema, M. W.; Wilson, P. D.; Audrain, H.; Fallis, A. G. Can. J. Chem. 1997, 75, 1215. (f) Dai, W.-M.; Lau, C. W.; Chung, S. H.; Wu, Y. D. J. Org. Chem. 1995, 60, 8128. (g) Graziano, M.; Iesce, M. R.; Cermola, F. Synthesis 1994, 149. (h) Nicolaou, K. C.; Hwang, C. K.; Sorensen, E. J.; Clairborne, C. F. J. Chem. Soc., Chem. Commun. 1992, 1117. (i) Bonnert, R. V.; Jenkins, P. R. Tetrahedron Lett. 1987, 28, 697. (j) Erman, W. F.; Stone, L. C. J. Am. Chem. Soc. 1971, 93, 2821.
17. For the Diels-Alder reactions with highly substituted 1,3-dienes see: (a) Schmittel, M.; Von Seggern, H. J. Am. Chem. Soc. 1993, 115, 2165. (b) Wehbe, M.; Lepage, L.; Lepage, Y.; Platzer, N. Bull. Soc. Chim. Fr. 1987, 309. (c) Majo, V. J.; Suzuki, S.; Toyota, M.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 2000, 3375. (d) Phansavath, P.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1998, 39, 1561. (e) Tjepkema, M. W.; Wilson, P. D.; Audrain, H.; Fallis, A. G. Can. J. Chem. 1997, 75, 1215. (f) Dai, W.-M.; Lau, C. W.; Chung, S. H.; Wu, Y. D. J. Org. Chem. 1995, 60, 8128. (g) Graziano, M.; Iesce, M. R.; Cermola, F. Synthesis 1994, 149. (h) Nicolaou, K. C.; Hwang, C. K.; Sorensen, E. J.; Clairborne, C. F. J. Chem. Soc., Chem. Commun. 1992, 1117. (i) Bonnert, R. V.; Jenkins, P. R. Tetrahedron Lett. 1987, 28, 697. (j) Erman, W. F.; Stone, L. C. J. Am. Chem. Soc. 1971, 93, 2821.
18. For the Diels-Alder reactions with highly substituted 1,3-dienes see: (a) Schmittel, M.; Von Seggern, H. J. Am. Chem. Soc. 1993, 115, 2165. (b) Wehbe, M.; Lepage, L.; Lepage, Y.; Platzer, N. Bull. Soc. Chim. Fr. 1987, 309. (c) Majo, V. J.; Suzuki, S.; Toyota, M.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 2000, 3375. (d) Phansavath, P.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1998, 39, 1561. (e) Tjepkema, M. W.; Wilson, P. D.; Audrain, H.; Fallis, A. G. Can. J. Chem. 1997, 75, 1215. (f) Dai, W.-M.; Lau, C. W.; Chung, S. H.; Wu, Y. D. J. Org. Chem. 1995, 60, 8128. (g) Graziano, M.; Iesce, M. R.; Cermola, F. Synthesis 1994, 149. (h) Nicolaou, K. C.; Hwang, C. K.; Sorensen, E. J.; Clairborne, C. F. J. Chem. Soc., Chem. Commun. 1992, 1117. (i) Bonnert, R. V.; Jenkins, P. R. Tetrahedron Lett. 1987, 28, 697. (j) Erman, W. F.; Stone, L. C. J. Am. Chem. Soc. 1971, 93, 2821.
19. For the Diels-Alder reactions with highly substituted 1,3-dienes see: (a) Schmittel, M.; Von Seggern, H. J. Am. Chem. Soc. 1993, 115, 2165. (b) Wehbe, M.; Lepage, L.; Lepage, Y.; Platzer, N. Bull. Soc. Chim. Fr. 1987, 309. (c) Majo, V. J.; Suzuki, S.; Toyota, M.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 2000, 3375. (d) Phansavath, P.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1998, 39, 1561. (e) Tjepkema, M. W.; Wilson, P. D.; Audrain, H.; Fallis, A. G. Can. J. Chem. 1997, 75, 1215. (f) Dai, W.-M.; Lau, C. W.; Chung, S. H.; Wu, Y. D. J. Org. Chem. 1995, 60, 8128. (g) Graziano, M.; Iesce, M. R.; Cermola, F. Synthesis 1994, 149. (h) Nicolaou, K. C.; Hwang, C. K.; Sorensen, E. J.; Clairborne, C. F. J. Chem. Soc., Chem. Commun. 1992, 1117. (i) Bonnert, R. V.; Jenkins, P. R. Tetrahedron Lett. 1987, 28, 697. (j) Erman, W. F.; Stone, L. C. J. Am. Chem. Soc. 1971, 93, 2821.
20. For the Diels-Alder reactions with highly substituted 1,3-dienes see: (a) Schmittel, M.; Von Seggern, H. J. Am. Chem. Soc. 1993, 115, 2165. (b) Wehbe, M.; Lepage, L.; Lepage, Y.; Platzer, N. Bull. Soc. Chim. Fr. 1987, 309. (c) Majo, V. J.; Suzuki, S.; Toyota, M.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 2000, 3375. (d) Phansavath, P.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1998, 39, 1561. (e) Tjepkema, M. W.; Wilson, P. D.; Audrain, H.; Fallis, A. G. Can. J. Chem. 1997, 75, 1215. (f) Dai, W.-M.; Lau, C. W.; Chung, S. H.; Wu, Y. D. J. Org. Chem. 1995, 60, 8128. (g) Graziano, M.; Iesce, M. R.; Cermola, F. Synthesis 1994, 149. (h) Nicolaou, K. C.; Hwang, C. K.; Sorensen, E. J.; Clairborne, C. F. J. Chem. Soc., Chem. Commun. 1992, 1117. (i) Bonnert, R. V.; Jenkins, P. R. Tetrahedron Lett. 1987, 28, 697. (j) Erman, W. F.; Stone, L. C. J. Am. Chem. Soc. 1971, 93, 2821.
21. For the Diels-Alder reactions with highly substituted 1,3-dienes see: (a) Schmittel, M.; Von Seggern, H. J. Am. Chem. Soc. 1993, 115, 2165. (b) Wehbe, M.; Lepage, L.; Lepage, Y.; Platzer, N. Bull. Soc. Chim. Fr. 1987, 309. (c) Majo, V. J.; Suzuki, S.; Toyota, M.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 2000, 3375. (d) Phansavath, P.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1998, 39, 1561. (e) Tjepkema, M. W.; Wilson, P. D.; Audrain, H.; Fallis, A. G. Can. J. Chem. 1997, 75, 1215. (f) Dai, W.-M.; Lau, C. W.; Chung, S. H.; Wu, Y. D. J. Org. Chem. 1995, 60, 8128. (g) Graziano, M.; Iesce, M. R.; Cermola, F. Synthesis 1994, 149. (h) Nicolaou, K. C.; Hwang, C. K.; Sorensen, E. J.; Clairborne, C. F. J. Chem. Soc., Chem. Commun. 1992, 1117. (i) Bonnert, R. V.; Jenkins, P. R. Tetrahedron Lett. 1987, 28, 697. (j) Erman, W. F.; Stone, L. C. J. Am. Chem. Soc. 1971, 93, 2821.
22. For the Diels-Alder reactions with highly substituted 1,3-dienes see: (a) Schmittel, M.; Von Seggern, H. J. Am. Chem. Soc. 1993, 115, 2165. (b) Wehbe, M.; Lepage, L.; Lepage, Y.; Platzer, N. Bull. Soc. Chim. Fr. 1987, 309. (c) Majo, V. J.; Suzuki, S.; Toyota, M.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 2000, 3375. (d) Phansavath, P.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1998, 39, 1561. (e) Tjepkema, M. W.; Wilson, P. D.; Audrain, H.; Fallis, A. G. Can. J. Chem. 1997, 75, 1215. (f) Dai, W.-M.; Lau, C. W.; Chung, S. H.; Wu, Y. D. J. Org. Chem. 1995, 60, 8128. (g) Graziano, M.; Iesce, M. R.; Cermola, F. Synthesis 1994, 149. (h) Nicolaou, K. C.; Hwang, C. K.; Sorensen, E. J.; Clairborne, C. F. J. Chem. Soc., Chem. Commun. 1992, 1117. (i) Bonnert, R. V.; Jenkins, P. R. Tetrahedron Lett. 1987, 28, 697. (j) Erman, W. F.; Stone, L. C. J. Am. Chem. Soc. 1971, 93, 2821.
23. For the Diels-Alder reactions with highly substituted 1,3-dienes see: (a) Schmittel, M.; Von Seggern, H. J. Am. Chem. Soc. 1993, 115, 2165. (b) Wehbe, M.; Lepage, L.; Lepage, Y.; Platzer, N. Bull. Soc. Chim. Fr. 1987, 309. (c) Majo, V. J.; Suzuki, S.; Toyota, M.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 2000, 3375. (d) Phansavath, P.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1998, 39, 1561. (e) Tjepkema, M. W.; Wilson, P. D.; Audrain, H.; Fallis, A. G. Can. J. Chem. 1997, 75, 1215. (f) Dai, W.-M.; Lau, C. W.; Chung, S. H.; Wu, Y. D. J. Org. Chem. 1995, 60, 8128. (g) Graziano, M.; Iesce, M. R.; Cermola, F. Synthesis 1994, 149. (h) Nicolaou, K. C.; Hwang, C. K.; Sorensen, E. J.; Clairborne, C. F. J. Chem. Soc., Chem. Commun. 1992, 1117. (i) Bonnert, R. V.; Jenkins, P. R. Tetrahedron Lett. 1987, 28, 697. (j) Erman, W. F.; Stone, L. C. J. Am. Chem. Soc. 1971, 93, 2821.
24. As main product of the reactions, the corresponding aromatic boronic ester (2-(2-isopropenyl-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan was isolated.
25. Generally the allylboration of the aldehydes was performed at 40 °C. The conversion with paraformaldehyde was performed successfully at 100°C in a thick-walled glass tube; compare to: (a) Kalinin, A. V.; Scherer, S.; Snieckus, V. Angew. Chem. 2003, 115, 3521; Angew. Chem., Int. Ed. 2003, 42, 3399. (b) Hoffmann, R. W.; Menzel, K.; Harms, K. Eur. J. Org. Chem. 2002, 2603.
26. Generally the allylboration of the aldehydes was performed at 40 °C. The conversion with paraformaldehyde was performed successfully at 100°C in a thick-walled glass tube; compare to: (a) Kalinin, A. V.; Scherer, S.; Snieckus, V. Angew. Chem. 2003, 115, 3521; Angew. Chem., Int. Ed. 2003, 42, 3399. (b) Hoffmann, R. W.; Menzel, K.; Harms, K. Eur. J. Org. Chem. 2002, 2603.
27. Generally the allylboration of the aldehydes was performed at 40 °C. The conversion with paraformaldehyde was performed successfully at 100°C in a thick-walled glass tube; compare to: (a) Kalinin, A. V.; Scherer, S.; Snieckus, V. Angew. Chem. 2003, 115, 3521; Angew. Chem., Int. Ed. 2003, 42, 3399. (b) Hoffmann, R. W.; Menzel, K.; Harms, K. Eur. J. Org. Chem. 2002, 2603.
28. The X-ray data were deposited in the CCDC data bank (CCDC 246015).