Cu(OTf)2-catalyzed isomerization of 7-oxabicyclic alkenes: A practical route to the synthesis of 1-naphthol derivatives

Synthesis

Volumn , Issue 19, 2008, Pages 3043-3046

  Peng, Fangzhi ^a   Fan, Baomin ^a   Shao, Zhihui ^a   Pu, Xuewei ^a   Li, Penghui ^a   Zhang, Hongbin ^a  

^a YUNNAN UNIVERSITY   (China)

Author keywords

1 naphthol derivative; 7 oxabicyclic alkenes; Catalysis; Copper; Isomerization

Indexed keywords

ACIDS; COPPER; HYDROCARBONS; OLEFINS;

1-NAPHTHOL DERIVATIVE; 7-OXABICYCLIC ALKENES; CATALYSIS; ISOMERIZATION;

PHENOLS;

1 NAPHTHOL DERIVATIVE; 7 OXABICYCLIC ALKENE; ALKENE; COPPER COMPLEX; LEWIS ACID; NORBORNADIENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERIZATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 53949121374     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067268     Document Type: Article

References (26)

1. Fangzhi Peng and Baomin Fan contributed equally to this study
2. Wittig, G.; Pohmer, L. Chem. Ber. 1956, 89, 1349.
3. Bart, D. G.; Jones, D. G.; Greca, S. L. J. Org. Chem. 1991, 56, 6704.
4. Olthuisb, E.; Ossenbroegko, Y.; Ewall, R.; Eels, E. D.; Leegwat, A. J. Org. Chem. 1963, 28, 148.
5. Kaelin, D. E.; Lopez, O.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937.
6. Apsel, B.; Bender, J. A.; Escobar, M.; Kaelin, D. E.; Lopez, O. D.; Martin, S. F. Tetrahedron Lett. 2003, 44, 1075.
7. Kaelin, D. E.; Sparks, S. M.; Plake, H. R.; Martin, S. F. J. Am. Chem. Soc. 2003, 125, 12994.
8. Biland-Thommen, A. S.; Raju, G. S.; Blagg, J.; White, A. J. F.; Barrett, A. G. M. Tetrahedron Lett. 2004, 45, 3181.
9. Terao, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2000, 56, 1315.
10. Chen, C. L.; Martin, S. F. J. Org. Chem. 2006, 71, 4810.
11. Yamamoto, H. Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, 2000.
12. Kobayashi, S.; Ogino, T.; Shimizu, H.; Ishikawa, S.; Hamada, T.; Manabe, K. Org. Lett. 2005, 7, 4729.
13. Curini, M.; Epifano, F.; Genovese, S.; Marcotullio, M. C.; Rosati, O. Org. Lett. 2005, 7, 1331.
14. Deng, X. M.; Sun, X. L.; Tang, Y. J. J. Org. Chem. 2005, 70, 6537.
15. Lacey, J. R.; Anzalone, P. W.; Duncan, C. M.; Hackert, M. J.; Mohan, R. S. Tetrahedron Lett. 2005, 46, 8507.
16. Ollevier, T.; Nadeau, E. Synlett 2006, 219.
17. Kang, Y. B.; Tang, Y.; Sun, X. L. Org. Biomol. Chem. 2006, 4, 299.
18. Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. L. Chem. Rev. 2002, 102, 2227.
19. Villeneuve, K.; Tam, W. J. Am. Chem. Soc. 2006, 128, 3514.
20. Dodge, J. A.; Chamberlin, A. R. Tetrahedron Lett. 1988, 29, 4827.
21. Baa, D. G. Eur. Pat. Appl. EP 2011071, 1987.
22. Bohhnann, F.; Zdero, C. Chem. Ber. 1976, 109, 2021.
23. Bohhnann, F.; Mailahn, W. Chem. Ber. 1981, 114, 1091.
24. Adachi, K.; Taniguchi, N. Bull. Chem. Soc. Jpn. 1982, 55, 1655.
25. Adachi, K.; Masahito, M. Bull. Chem. Soc. Jpn. 1983, 56, 651.
26. Zhang, T. K.; Yuan, K.; Hou, X. L. J. Organomet. Chem. 2007, 692, 1912.