A novel one-pot cycloisomerization-Wittig sequence with yne-allyl alcohols

Synlett

Volumn , Issue 4, 2004, Pages 655-658

  Kressierer, Christoph J ^a   Müller, Thomas J J ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Alkynes; Catalysis; Domino reactions; Ene reactions; Wittig reactions

Indexed keywords

ALCOHOL DERIVATIVE; PALLADIUM; PHOSPHORUS;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; ISOMERIZATION; OLEFINATION; REACTION ANALYSIS; WITTIG REACTION;

EID: 1642335402     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817768     Document Type: Article

References (28)

1. For recent excellent reviews on transition metal-assisted sequential transformations and domino processes, see e.g.: (a) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (c) Negishi, E.-I.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. Tietze, L. F. Chem. Rev. 1996, 96, 115.
2. For recent excellent reviews on transition metal-assisted sequential transformations and domino processes, see e.g.: (a) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (c) Negishi, E.-I.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. Tietze, L. F. Chem. Rev. 1996, 96, 115.
3. For recent excellent reviews on transition metal-assisted sequential transformations and domino processes, see e.g.: (a) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (c) Negishi, E.-I.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. Tietze, L. F. Chem. Rev. 1996, 96, 115.
4. For recent excellent reviews on transition metal-assisted sequential transformations and domino processes, see e.g.: (a) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (c) Negishi, E.-I.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. (d) Tietze, L. F. Chem. Rev. 1996, 96, 115.
5. For representative transition metal catalyzed Alder-ene reactions, see e.g.: (a) Pd: Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Pd: Trost, B. M. Janssen Chim. Acta 1991, 9, 3. (c) Pd: Trost, B. M.; Krische, M. J. Synlett 1998, 1. (d) Ru: Trost, B. M. Chem. Ber. 1996, 129, 1313. (e) Ru: Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739. (f) Rh: Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490. (g) Rh: Cao, P.; Zhang, X. Angew. Chem. Int. Ed. 2000, 22, 4104. (h) Rh: Lei, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198. Ir: Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433. (j) Ti: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
6. For representative transition metal catalyzed Alder-ene reactions, see e.g.: (a) Pd: Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Pd: Trost, B. M. Janssen Chim. Acta 1991, 9, 3. (c) Pd: Trost, B. M.; Krische, M. J. Synlett 1998, 1. (d) Ru: Trost, B. M. Chem. Ber. 1996, 129, 1313. (e) Ru: Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739. (f) Rh: Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490. (g) Rh: Cao, P.; Zhang, X. Angew. Chem. Int. Ed. 2000, 22, 4104. (h) Rh: Lei, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198. Ir: Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433. (j) Ti: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
7. For representative transition metal catalyzed Alder-ene reactions, see e.g.: (a) Pd: Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Pd: Trost, B. M. Janssen Chim. Acta 1991, 9, 3. (c) Pd: Trost, B. M.; Krische, M. J. Synlett 1998, 1. (d) Ru: Trost, B. M. Chem. Ber. 1996, 129, 1313. (e) Ru: Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739. (f) Rh: Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490. (g) Rh: Cao, P.; Zhang, X. Angew. Chem. Int. Ed. 2000, 22, 4104. (h) Rh: Lei, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198. Ir: Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433. (j) Ti: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
8. For representative transition metal catalyzed Alder-ene reactions, see e.g.: (a) Pd: Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Pd: Trost, B. M. Janssen Chim. Acta 1991, 9, 3. (c) Pd: Trost, B. M.; Krische, M. J. Synlett 1998, 1. (d) Ru: Trost, B. M. Chem. Ber. 1996, 129, 1313. (e) Ru: Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739. (f) Rh: Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490. (g) Rh: Cao, P.; Zhang, X. Angew. Chem. Int. Ed. 2000, 22, 4104. (h) Rh: Lei, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198. Ir: Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433. (j) Ti: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
9. For representative transition metal catalyzed Alder-ene reactions, see e.g.: (a) Pd: Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Pd: Trost, B. M. Janssen Chim. Acta 1991, 9, 3. (c) Pd: Trost, B. M.; Krische, M. J. Synlett 1998, 1. (d) Ru: Trost, B. M. Chem. Ber. 1996, 129, 1313. (e) Ru: Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739. (f) Rh: Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490. (g) Rh: Cao, P.; Zhang, X. Angew. Chem. Int. Ed. 2000, 22, 4104. (h) Rh: Lei, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198. Ir: Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433. (j) Ti: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
10. For representative transition metal catalyzed Alder-ene reactions, see e.g.: (a) Pd: Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Pd: Trost, B. M. Janssen Chim. Acta 1991, 9, 3. (c) Pd: Trost, B. M.; Krische, M. J. Synlett 1998, 1. (d) Ru: Trost, B. M. Chem. Ber. 1996, 129, 1313. (e) Ru: Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739. (f) Rh: Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490. (g) Rh: Cao, P.; Zhang, X. Angew. Chem. Int. Ed. 2000, 22, 4104. (h) Rh: Lei, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198. Ir: Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433. (j) Ti: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
11. For representative transition metal catalyzed Alder-ene reactions, see e.g.: (a) Pd: Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Pd: Trost, B. M. Janssen Chim. Acta 1991, 9, 3. (c) Pd: Trost, B. M.; Krische, M. J. Synlett 1998, 1. (d) Ru: Trost, B. M. Chem. Ber. 1996, 129, 1313. (e) Ru: Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739. (f) Rh: Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490. (g) Rh: Cao, P.; Zhang, X. Angew. Chem. Int. Ed. 2000, 22, 4104. (h) Rh: Lei, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198. Ir: Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433. (j) Ti: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
12. For representative transition metal catalyzed Alder-ene reactions, see e.g.: (a) Pd: Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Pd: Trost, B. M. Janssen Chim. Acta 1991, 9, 3. (c) Pd: Trost, B. M.; Krische, M. J. Synlett 1998, 1. (d) Ru: Trost, B. M. Chem. Ber. 1996, 129, 1313. (e) Ru: Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739. (f) Rh: Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490. (g) Rh: Cao, P.; Zhang, X. Angew. Chem. Int. Ed. 2000, 22, 4104. (h) Rh: Lei, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198. Ir: Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433. (j) Ti: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
13. For representative transition metal catalyzed Alder-ene reactions, see e.g.: (a) Pd: Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Pd: Trost, B. M. Janssen Chim. Acta 1991, 9, 3. (c) Pd: Trost, B. M.; Krische, M. J. Synlett 1998, 1. (d) Ru: Trost, B. M. Chem. Ber. 1996, 129, 1313. (e) Ru: Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739. (f) Rh: Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490. (g) Rh: Cao, P.; Zhang, X. Angew. Chem. Int. Ed. 2000, 22, 4104. (h) Rh: Lei, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198. (i) Ir: Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433. (j) Ti: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
14. For representative transition metal catalyzed Alder-ene reactions, see e.g.: (a) Pd: Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Pd: Trost, B. M. Janssen Chim. Acta 1991, 9, 3. (c) Pd: Trost, B. M.; Krische, M. J. Synlett 1998, 1. (d) Ru: Trost, B. M. Chem. Ber. 1996, 129, 1313. (e) Ru: Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739. (f) Rh: Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490. (g) Rh: Cao, P.; Zhang, X. Angew. Chem. Int. Ed. 2000, 22, 4104. (h) Rh: Lei, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198. Ir: Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433. (j) Ti: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
15. For leading reviews on Pd catalyzed cycloisomerizations, see, e.g.: (a) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 215.
16. (b) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
17. (a) Karpov, A. S.; Rominger, F.; Müller, T. J. J. J. Org. Chem. 2003, 68, 1503.
18. (b) Yehia, N. A. M.; Polborn, K.; Müller, T. J. J. Tetrahedron Lett. 2002, 43, 6907.
19. (c) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297.
20. (d) Müller, T. J. J.; Robert, J. P.; Schmälzlin, E.; Bräuchle, C.; Meerholz, K. Org. Lett. 2000, 2, 2419.
21. (e) Müller, T. J. J.; Ansorge, M.; Aktah, D. Angew. Chem. Int. Ed. 2000, 39, 1253.
22. (a) Trost, B. M.; Li, Y. J. Am. Chem. Soc. 1996, 118, 6625.
23. (b) Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027.
24. (6) (a) The synthesis of yne allyl alcohol substrates were performed according to: Sajiki, H.; Hirota, K. Tetrahedron 1998, 54, 13981.
25. (b) The detailed protocols will be described elsewhere.
26. 5Si: 312.1393; found: 312.1397.
27. All compounds have been fully characterized spectroscopically and by correct elemental analysis or HRMS.
28. 6: 386.1729; found: 386.1735.