Diastereoselective dearomatization of resorcinols directed by a lactic acid tether: Unprecedented enantioselective access to p-quinols

Organic Letters

Volumn 6, Issue 10, 2004, Pages 1535-1538

  Mejorado, Lupe H ^a   Hoarau, Christophe ^a   Pettus, Thomas R R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE DERIVATIVE; CYCLOHEXENE DERIVATIVE; LACTIC ACID; RESORCINOL DERIVATIVE;

AROMATIZATION; ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; OXIDATION; STEREOCHEMISTRY;

HYDROQUINONES; LACTIC ACID; MOLECULAR STRUCTURE; RESORCINOLS; STEREOISOMERISM;

EID: 2542513317     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0498592     Document Type: Article

References (28)

1. Magdziak, D.; Meek, S.; Pettus, T. R. R. Chem. Rev. 2004, 104, 1383-1429.
2. Fujioka, H.; Annoura, H.; Murano, K.; Kita, Y.; Tamura, Y. Chem Pharm Bull. 1989, 37, 2047-2052.
3. Murakata, M.; Yamada, K.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1994, 443-444.
4. Myers, A. G.; Siegel, D. R.; Buzzard, D. J.; Charest, M. G. Org. Lett. 2001, 3, 2923-2926.
5. Kneifel, H.; Poszich-Buscher, C.; Rittich, S.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1991, 30, 202-203.
6. Corey, E. J.; Wu, L. I. J. Am. Chem. Soc. 1993, 115, 9327-9328.
7. Wipf, P.; Kim, Y.; Jahn, H. Synthesis 1995, 1549-1561.
8. Hu, Y.; Li, C.; Kulkarni, B. A.; Strobel, G.; Lobkovsky, E.; Torczynski, R. M.; Porco, J. A., Jr. Org. Lett. 2001, 3, 1649-1652.
9. Genski, T.; Macdonald, G.; Wei, X.; Lewis, N.; Taylor, R. J. K. Synlett 1999, 795-797.
10. Imbos, R.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2001, 57, 2485-2489.
11. de March, P.; Escoda, M.; Figueredo, M.; Font, J.; Garcia-Garcia, E.; Rodriguez, S. Tetrahedron: Asymmetry 2000, 11, 4473-4483.
12. Wolter, M.; Borm, C.; Merten, E.; Wartchow, R.; Winterfeldt, E. Eur. J. Org. Chem. 2001, 4051-4060.
13. Carreno, M. C.; Gonzalez, M. P.; Fisher, J. Tetrahedron Lett. 1995, 36, 4893-4896.
14. Wipf, P.; Jung, J.-K. J. Org. Chem. 2000, 65, 6319-6337.
15. Breuning, M.; Corey, E. J. Org. Lett. 2001, 3, 1559-1562.
16. Gerstenberger, I.; Hansen, M.; Mauvais, A.; Wartchow, R.; Winterfeldt, E. Eur. J. Org. Chem. 1998, 643, 3-650.
17. Imbos, R.; Brilman, M. H. G.; Pineschi, M.; Feringa, B. L. Org. Lett. 1999, 1, 623-625.
18. (a) Van De Water, R. W.; Hoarau, C.; Pettus, T. R. R. Tetrahedron Lett. 2003, 44, 5109-5113.
19. (b) Pettus, L. H.; Van De Water, R. W.; Pettus, T. R. R. Org. Lett. 2001, 3, 905-908.
20. (a) Van De Water, R. W.; Magdziak, D. J.; Chau, J. N.; Pettus, T. R. R. J. Am. Chem. Soc. 2000, 122, 6502-6503.
21. (b) Jones, R.; Van De Water, R. W.; Lindsey, C.; Hoarau, C.; Ung; T.; Pettus, T. R. R. J. Org. Chem. 2001, 66, 3435-3441.
22. (c) Hoarau, C.; Pettus, T. R. R. Synlett 2003, 127.
23. (d) Tuttle, K.; Pettus, T. R. R. Synlett 2003, 2234-2236.
24. (e) Lindsey, C.; Gomez-Diaz, C.; Villalba, J. M.; Pettus, T. R. R. Tetrahedron 2002, 58, 4559-4565.
25. Bui, E.; Bayle, J. P.; Perez, F.; Liebert, L.; Courtieu, J. Liquid Crystals 1990, 8, 513-526.
26. (a) Paterson, I.; Wallace, D. J.; Cowden, C. J. Synthesis 1998, 639-652.
27. (b) Less, S. L.; Leadlay, P. F.; Dutton, C. J.; Staunton, J. Tetrahedron Lett. 1996, 37, 3519-3520.
28. Murakata, M.; Yamada, K.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1994, 443-445.