Short and efficient diastereoselective synthesis of enantiopure 1-substituted 1H-2-benzopyrans

European Journal of Organic Chemistry

Volumn , Issue 22, 2006, Pages 5110-5116

  Pedrosa, Rafael ^a   Sayalero, Sonia ^a,b   Vicente, Martina ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

1,3 Amino alcohols; Asymmetric synthesis; Benzopyrans; Isochromanes; Isochromenes

Indexed keywords

EID: 33751309404     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600585     Document Type: Article

References (31)

1. a) J. M. Grisar, M. A. Petty, F. N. Bolkenius, J. Dow, J. Wagner, E. R. Wagner, K. D. Haegele, W. D. Jung, J. Med. Chem. 1991, 34, 257;
2. b) H. Laatsch, Angew. Chem. Int. Ed. Engl. 1994, 33, 422;
3. c) N. P. Seeran, H. Jacobs, S. McLean, W. F. Reynolds, Phytochemistry 1998, 49, 1389;
4. d) T. Tanaka, F. Asai, M. Iinuma, Phytochemistry 1998, 49, 229.
5. a) O. Potterat, H. Zahner, C. Volkmann, A. Zeeck, J. Antibiotic 1993, 46, 346;
6. b) A. Ali, R. W. Read, S. Sotheeswaran, Phytochemistry 1994, 35, 1029;
7. c) L. Hari, L. F. de Buyck, H. L. de Pooter, Phytochemistry 1991, 30, 1726;
8. d) G. K. Poch, J. B. Gloer, Tetrahedron Lett. 1989, 30, 3483.
9. J. D. Hepworth in Comprehensive Heterocyclic Chemistry (Ed.: A. R. Katritzky), Pergamon, 1984, vol. 3, chapter 2, p. 765.
10. J. Thibault, Ann. Chim. 1971, 6, 381.
11. R. Hug, H.-J. Hansen, H. Schmid, Helv. Chim. Acta 1972, 55, 10.
12. F. Léost, B. Chantegrel, C. Deshayes, Tetrahedron 1998, 54, 6457.
13. B. Wünsch, Arch. Pharm. 1990, 323, 493.
14. R. Mutter, I. B. Campbell, E. M. Martin, A. T. Merritt, M. Wills, J. Org. Chem. 2001, 66, 3284.
15. B. Gabriele, G. Salerno, A. Fazio, R. Pittelli, Tetrahedron 2003, 59, 6251.
16. R. G. F. Gilet, I. R. Green, C. P. Taylor, Tetrahedron Lett. 1999, 40, 4871.
17. N. Asao, T. Nogami, K. Takahashi, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 764.
18. J. Barluenga, H. Vázquez-Villa, A. Ballesteros, J. M. González, J. Am. Chem. Soc. 2003, 125, 9028.
19. D. Yue, N. Della Cá, R. C. Larock, J. Org. Chem. 2006, 71, 3381.
20. R. Pedrosa, S. Sayalero, M. Vicente, B. Casado, J. Org. Chem. 2005, 70, 7273.
21. A. Rassat, P. Rey, Tetrahedron 1974, 30, 3315.
22. W. S. Knowles, Q. E. Thompson, J. Org. Chem. 1960, 25, 1031.
23. Compound 5 was quantitatively obtained from 3 by reduction with sodium borohydride.
24. M. S. Karasch, O. Reinmuth in Grignard Reactions of Nonmetallic Substances, Prentice Hall, New York, 1954.
25. H.-J. Liu, K.-S. Shia, X. Shang, B.-Y. Zhu, Tetrahedron 1999, 55, 3803.
26. CCDC-619877 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
27. a) E. L. Eliel, S. Morris-Natschke, J. Am. Chem. Soc. 1984, 106, 2937;
28. b) X.-C. He, E. L. Eliel, Tetrahedron 1987, 43, 4979;
29. c) E. L. Eliel, X.-C. He, J. Org. Chem. 1990, 55, 2144.
30. J. Barluenga, J. R. Fernández, C. M. Rubiera, M. A. Yus, J. Chem. Soc. Perkin Trans. 1 1988, 3113.
31. K. J. Eash, M. S. Pulia, L. C. Wieland, R. S. Mohan, J. Org. Chem. 2000, 65, 8399.