2H-chromenes from salicylaldehydes by a catalytic petasis reaction

Organic Letters

Volumn 2, Issue 25, 2000, Pages 4063-4065

  Wang, Qian ^a   Finn, M G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000208180     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006710r     Document Type: Article

References (29)

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12. Imine formation from salicylaldehydes is particularly facile: Green, R. W.; Sleet, R. J. Aust. J. Chem. 1969, 22, 917-919.
13. (a) Petasis, N. A.; Boral, S.; Zavialov, I. A. Abstracts of Papers, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 1999; American Chemical Society: Washington, D.C., 1999; ORGN 083.
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15. Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1973, 95, 5786-5788.
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17. Equivalents of 8 vs yields of 5a, obtained after 12 h reaction: 0.05, 20%; 0.10, 68%; 0.20, 75%; 0.30, 87%; 0.40, 95%.
18. Some recent examples: (a) Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Angew. Chem., Int. Ed. 2000, 39, 734-739. Nicolaou, K. C.; Cao, G.-Q.; Pfefferkorn, J. A. Angew. Chem., Int. Ed. 2000, 39, 739-743.
19. Some recent examples: (a) Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Angew. Chem., Int. Ed. 2000, 39, 734-739. Nicolaou, K. C.; Cao, G.-Q.; Pfefferkorn, J. A. Angew. Chem., Int. Ed. 2000, 39, 739-743.
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23. (e) Engler, T. A.; Letavic, M. A.; Iyengar, R.; LaTessa, K. O.; Reddy, J. P. J. Org. Chem. 1999, 64, 2391-2405.
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26. (a) Harrity, J. P. A.; La, S. D.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H.; J. Am. Chem. Soc. 1998, 120, 2343-2351. This method was used for the synthesis of an antibiotic: Wipf, P.; Weiner, W. S. J. Org. Chem. 1999, 64, 5321-5324.
27. (a) Harrity, J. P. A.; La, S. D.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H.; J. Am. Chem. Soc. 1998, 120, 2343-2351. This method was used for the synthesis of an antibiotic: Wipf, P.; Weiner, W. S. J. Org. Chem. 1999, 64, 5321-5324.
28. (b) An alternative preparation of 2H-chromenes from salicyaldehydes employs nitroalkenes as the active olefin component; conjugate addition of the phenolate anion is followed by a second addition-elimination step using cyanide: Tronchet, J. M. J.; Zerelli, S.; Bernardinelli, G. J. Carbohydr. Chem. 1999, 18, 343-359.
29. (c) Catalytic antibodies have been developed to promote phenolic cyclization reactions to give chroman derivatives: Tietze, L. F.; Peters, J. H.; Djalali, B. F.; Seibel, J. Ger. Offen. DE 19852905 A1 20000511, 2000; Chem. Abstr. 2000, 132, 333447 (AN 315046).