Temperature- and time-dependent stereochemical control in thermally induced keto-ene cyclizations

Journal of Organic Chemistry

Volumn 68, Issue 5, 2003, Pages 1852-1858

  Pedrosa, Rafael ^a   Andrés, Celia ^a   Rosón, Carlos D ^a   Vicente, Martina ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

STEREOCHEMICAL CONTROL;

BENZENE; ISOMERS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

KETONES;

ALLYL COMPOUND; BENZOXAZINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; STEREOCHEMISTRY; TEMPERATURE; TIME;

EID: 0037424311     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026525m     Document Type: Article

References (25)

1. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 2, p 527.
2. (a) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. (b) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
3. (a) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. (b) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
4. Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. N. J. Am. Chem. Soc. 1998, 120, 5824.
5. Marshall, J. A.; Andersen, M. W. J. Org. Chem. 1993, 58, 3912.
6. (a) Alcaide, B.; Pardo, C.; Rodríguez-Ranera, C.; Rodríguez-Vicente, A. Org. Lett. 2001, 3, 4205. (b) Robertson, J.; O'Connor, G.; Ringrose, C. L.; Middleton, D. S. Tetrahedron 2000, 56, 8321. (c) Kocovsky, P.; Ahmed, G.; Srogl, J.; Malkov, A. V.; Steele, J. J. Org. Chem. 1999, 64, 2765 and references therein.
7. (a) Alcaide, B.; Pardo, C.; Rodríguez-Ranera, C.; Rodríguez-Vicente, A. Org. Lett. 2001, 3, 4205. (b) Robertson, J.; O'Connor, G.; Ringrose, C. L.; Middleton, D. S. Tetrahedron 2000, 56, 8321. (c) Kocovsky, P.; Ahmed, G.; Srogl, J.; Malkov, A. V.; Steele, J. J. Org. Chem. 1999, 64, 2765 and references therein.
8. (a) Alcaide, B.; Pardo, C.; Rodríguez-Ranera, C.; Rodríguez-Vicente, A. Org. Lett. 2001, 3, 4205. (b) Robertson, J.; O'Connor, G.; Ringrose, C. L.; Middleton, D. S. Tetrahedron 2000, 56, 8321. (c) Kocovsky, P.; Ahmed, G.; Srogl, J.; Malkov, A. V.; Steele, J. J. Org. Chem. 1999, 64, 2765 and references therein.
9. Hiersemann, M. Eur. J. Org. Chem. 2001, 483.
10. Cheung, C.-M.; Craig, D.; Todd, R. Synlett 2001, 1611.
11. Pedrosa, R.; Andrés, C.; Nieto, J. J. Org. Chem. 2002, 67, 782.
12. Pedrosa, R.; Andrés, C.; Iglesias, J. M.; Pérez-Encabo, A. J. Am. Chem. Soc. 2001, 123, 1817.
13. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282.
14. Pedrosa, R.; Andrés, C.; de las Heras, L.; Nieto, J. Org. Lett. 2002, 4, 2513.
15. See Supporting Information
16. (a) Andersen, N. H.; Hadley, S. W.; Kelly, J. D.; Bacon, E. R. J. Org. Chem. 1985, 50, 4144. (b) Paquette, L. A.; Annis, G. D. J. Am. Chem. Soc. 1983, 105, 7358. (c) Snider, B. B.; Karras, M.; Price, R. T.; Rodini, D. J. J. Org. Chem. 1982, 47, 4538.
17. (a) Andersen, N. H.; Hadley, S. W.; Kelly, J. D.; Bacon, E. R. J. Org. Chem. 1985, 50, 4144. (b) Paquette, L. A.; Annis, G. D. J. Am. Chem. Soc. 1983, 105, 7358. (c) Snider, B. B.; Karras, M.; Price, R. T.; Rodini, D. J. J. Org. Chem. 1982, 47, 4538.
18. (a) Andersen, N. H.; Hadley, S. W.; Kelly, J. D.; Bacon, E. R. J. Org. Chem. 1985, 50, 4144. (b) Paquette, L. A.; Annis, G. D. J. Am. Chem. Soc. 1983, 105, 7358. (c) Snider, B. B.; Karras, M.; Price, R. T.; Rodini, D. J. J. Org. Chem. 1982, 47, 4538.2
19. White, J. D.; Somers, T. C. J. Am. Chem. Soc. 1987, 109, 4424.
20. Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461.
21. (a) Warrington, J. M.; Yap, G. P. A.; Barriault, L. Org. Lett. 2000, 2, 663. (b) Ripoll, J. L.; Valée, Y. Synthesis 1993, 659.
22. (a) Warrington, J. M.; Yap, G. P. A.; Barriault, L. Org. Lett. 2000, 2, 663. (b) Ripoll, J. L.; Valée, Y. Synthesis 1993, 659.
23. (a) Loncharich, R. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 6947. (b) Oppolzer, W.; Pfenninger, E.; Keller, K. Helv. Chim. Acta 1973, 56, 1807.
24. (a) Loncharich, R. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 6947. (b) Oppolzer, W.; Pfenninger, E.; Keller, K. Helv. Chim. Acta 1973, 56, 1807.
25. Braddock, D. C.; Hii, K. K.; Brown, J. M. Angew. Chem., Int. Ed. 1998, 37, 1720.