Synthesis of 1,3-dihydrobenzo[c]furans from ortho-lithiated aryloxiranes

Journal of Organic Chemistry

Volumn 71, Issue 10, 2006, Pages 3984-3987

  Capriati, Vito ^a   Florio, Saverio ^a   Luisi, Renzo ^a   Perna, Filippo M ^a   Salomone, Antonio ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,3-DIHYDROBENZO[C]FURANS; CARBONYL COMPOUNDS; ORTHO-LITHIATED ARYLOXIRANES;

ESTERS; LITHIUM COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

1,3 DIHYDROBENZO[C]FURAN DERIVATIVE; BENZOFURAN DERIVATIVE; CARBONYL DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; LITHIUM; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; LITHIATION; REACTION ANALYSIS; STEREOSPECIFICITY; SUBSTITUTION REACTION;

EPOXY COMPOUNDS; FURANS; MOLECULAR STRUCTURE;

EID: 33646533099     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052645t     Document Type: Article

References (21)

1. (a) Lovey, R. G.; Elliott, A. J.; Kaminski, J. J.; Loebenberg, D.; Parmegiani, R. M.; Rane, D. F.; Girijavallabham, V. M.; Pike, R. E.; Guzik, H.; et al. J. Med. Chem. 1992, 35, 4221-4229.
2. (b) Ram, S.; Saxena, A. K.; Jain, P. C.; Patnaik, G. K. Indian J. Chem. Sect. B 1984, 23, 1261.
3. (c) Klohs, M. W.; Petracek, F. J. (Dart Industries Inc.). US Patent 3471519. 1969, 71, 124212.
4. (a) Sarkar, T. K.; Basak, S. Org. Lett. 2004, 6, 2925-2927.
5. (b) Fort, Y.; Gros, P.; Rodriguez, A. L. Tetrahedron Lett. 2002, 43, 4045-4048.
6. (c) Zemolka, S.; Lex, J.; Schmalz, H. Angew. Chem., Int. Ed. 2002, 41, 2525-2528.
7. (d) Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 2004, 104, 2667-2722.
8. (e) Coote, S. J.; Davies, S. G.; Middlemiss, D.; Naylor, A. J. Organomet. Chem. 1989, 379, 81-88.
9. (a) Parham, W. E.; Bradsher, C. K.; Reames, D. C. J. Org. Chem. 1981, 46, 4804-4806.
10. (b) Martin, C.; Mailliet, P.; Maddaluno, J. J. Org. Chem. 2001, 66, 3797-3805.
11. (c) Delacroix, T.; Bérillon, L.; Cahiez, G.; Knochel, P. J. Org. Chem. 2000, 65, 8108-8110.
12. (a) Ewing, D. F.; Len, C.; Mackenzie, G.; Ronco, G.; Villa, P. Tetrahedron: Asymmetry 2000, 11, 4995-5002.
13. (b) Tsukada, N.; Sugawara, S.; Nakaoka, K.; Inoue, Y. J. Org. Chem. 2003, 68, 5961-5966.
14. (a) Capriati, V.; Florio, S.; Luisi, R.; Perna, F. M.; Salomone, A.; Gasparrini, F. Org. Lett. 2005, 7, 4895-4898.
15. (b) Capriati, V.; Florio, S.; Luisi, R.; Musio, B. Org. Lett. 2005, 7, 3749-3752.
16. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-738.
17. (a) Beesley, R M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc. Trans. 1915, 107, 1080-1106.
18. (b) Ingold, C. K. Ibid. 1921, 119, 305-329.
19. Crystallographic data for compound 3a have been deposited at the Cambridge Crystallographic Data Centre (deposition no. CCDC-293337). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. [fax: (int.) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
20. Neuhaus, D.; Williamson, M. The Nuclear Overhauser Effect in Structural and Conformational Analysis; VCH: New York, 1989; p 264.
21. Parker, D. Chem. Rev. 1991, 91, 1441-1457.