Mild and stereoselective friedel-crafts alkylation of phenol derivatives with vinyloxiranes: A new access to cycloalkenobenzofurans

Synlett

Volumn , Issue 19, 2007, Pages 3011-3015

  Bertolini, Ferruccio ^a   Di Bussolo, Valeria ^a   Crotti, Paolo ^a   Pineschi, Mauro ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

Friedel Crafts; Fused ring systems; Regioselectivity; Stereoselectivity; Vinyloxiranes

Indexed keywords

CYCLOALKENOBENZOFURAN DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; FURAN DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG; VINYLOXIRANE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY;

EID: 37349025511     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-992353     Document Type: Article

References (28)

1. For recent examples, see: (a) Kimura, M.; Mukai, R.; Tamaki, T.; Horino, Y.; Tamaru, Y. J. Am. Chem. Soc. 2007, 129, 4122.
2. (b) Brunner, B.; Stogaitis, N.; Lautens, M. Org. Lett. 2006, 8, 3473.
3. (c) Charrier, N.; Gravestock, D.; Zard, S. Z. Angew. Chem. Int. Ed. 2006, 45, 6520.
4. (d) Restorp, P.; Somfai, P. Eur. J. Org. Chem. 2005, 3946; and references cited therein.
5. For a review, see: (a) Olah, G. A.; Krishnamurti, R.; Prakash, S. G. K. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 293.
6. For recent examples, see: (b) Bertolini, F.; Crotti, P.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 2006, 47, 61.
7. (c) Prakash, S. G. K.; Linares-Palomino, P. J.; Glinton, K.; Chacko, S.; Rasul, G.; Mathew, T.; Olah, G. A. Synlett 2007, 1158.
8. Vinyloxiranes have been used in an intramolecular process to control a 7-endo-selective Friedel-Crafts-type cyclization. See: Nagumo, S.; Miyoshi, I.; Akita, H.; Kawahara, N. Tetrahedron Lett. 2002, 43, 2223.
9. (a) Taylor, S. K.; Clark, D. L.; Heinz, K. L.; Schramm, S. B.; Westermann, C. D.; Barnell, K. K. J Org. Chem. 1983, 48, 592.
10. (b) The drastic reaction conditions used in this work, allowed direct ring opening of the oxirane ring by the Lewis acid promoter and caused the resulting alcohols to undergo a further Friedel-Crafts alkylation to give diarylated products.
11. 2O, see: Brandänge, S.; Bäckvall, J.-E.; Leijonmarck, H. J. Chem. Soc., Perkin Trans. 1 2001, 2051.
12. For the reactions of methyl 4,5-epoxypentenoate with aryl ethers, see: Ono, M.; Tanikawa, S.; Suzuki, K.; Akita, H. Tetrahedron 2004, 60, 10187; and references cited therein.
13. Pineschi, M.; Bertolini, F.; Haak, R. M.; Crotti, P.; Macchia, F. Chem. Commun. 2005, 1426.
14. Tsuji, Y.; Toteva Garth, H. A.; Richard, J. P. J. Am. Chem. Soc. 2003, 125, 15455.
15. For the use of indium salts in Friedel-Crafts-type reactions of heteroarenes with epoxides, see: (a) Yadav, J. S.; Reddy, B. V. S.; Parimala, G. Synlett 2002, 1143.
16. (b) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. J. Org. Chem. 2002, 67, 5386.
17. For the synthesis of tetrahydrobenzofurans, see: (a) Hosokawa, T.; Miyagi, S.; Murahashi, S.-I.; Sonoda, A. J. Org. Chem. 1978, 43, 2752.
18. (b) Guzzo, P. R.; Buckle, R. N.; Chou, M.; Dinn, S. R.; Flaugh, M. E.; Kiefer, A. D. Jr.; Ryter, K. T.; Sampognaro, A. J.; Tregay, S. W.; Xu, Y.-C. J. Org. Chem. 2003, 68, 770.
19. (c) Yamashita, M.; Inaba, T.; Nagahama, M.; Shimizu, T.; Kosaka, S.; Kawasaki, I.; Ohta, S. Org. Biomol. Chem. 2005, 3, 2296.
20. (d) Crich, D.; Sannigrahi, M. Tetrahedron 2002, 58, 3319.
21. For the obtainment of hexahydrodibenzofurans, see: (e) Liu, Q.; Han, B.; Zhang, W.; Yang, L.; Liu, Z.-L.; Yu, W. Synlett 2005, 2248.
22. (f) Kurono, N.; Honda, E.; Komatsu, F.; Orito, K.; Tokuda, M. Tetrahedron 2004, 60, 1791.
23. (g) Nguyen, R.-V.; Yao, X.; Li, C.-J. Org. Lett. 2006, 8, 2397.
24. (a) Clive, D. L. J.; Daigneault, S. J. Org. Chem. 1991, 56, 5285.
25. (b) Trost, B. M.; Tang, W.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 14785.
26. Aristoff, P. A.; Harrison, A. W.; Huber, A. M. Tetrahedron Lett. 1984, 25, 3955.
27. 3): δ = 24.7, 27.8, 39.8, 43.3, 55.1, 55.6, 71.1, 91.2, 94.4, 109.0, 132.1, 133.0, 156.3, 159.5, 159.7.
28. Brown, C. A.; Krishnamurthy, S. J. Org. Chem. 1978, 43, 2731.