Hetero-Diels-Alder reaction of photochemically generated α-hydroxy-o-quinodimethanes with trifluoromethyl ketones

Tetrahedron Letters

Volumn 53, Issue 31, 2012, Pages 3974-3976

  Takaki, Ken ^a   Fujii, Toshifumi ^a   Yonemitsu, Hosei ^a   Fujiwara, Makoto ^a   Komeyama, Kimihiro ^a   Yoshida, Hiroto ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Hydroxy o quinodimethanes; Hetero Diels Alder reaction; o Tolualdehydes; Photoreaction; Trifluoromethyl ketones

Indexed keywords

ALPHA HYDROXY ORTHO QUINODIMETHANE; HYDROXYALDEHYDE; KETONE DERIVATIVE; METHANE; TETRALIN DERIVATIVE; TRIFLUOROMETHYL KETONE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DIELS ALDER REACTION; OXIDATION; PHOTOCHEMISTRY;

ALNUS;

EID: 84862674410     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.05.082     Document Type: Article

References (13)

1. For reviews, see: J.L. Segura, and N. Martín Chem. Rev 99 1999 3199 3246
2. J.L. Charlton, and M.M. Alauddin Tetrahedron 43 1987 2873 2889
3. K.C. Nicolaou, and D.L.F. Gray J. Am. Chem. Soc. 126 2004 607 612
4. K.C. Nicolaou, D.L.F. Gray, and J. Tae J. Am. Chem. Soc. 126 2004 613 627
5. K. Benda, W. Regenhardt, E. Schaumann, and G. Adiwidjaja Eur. J. Org. Chem. 2009 1016 1021
6. M.F. Hentemann, J.G. Allen, and S.J. Danishefsky Angew. Chem., Int. Ed. 39 2000 1937 1940
7. D. Craig, M.J. Robson, and S.J. Shaw Synlett 1998 1381 1383
8. K. Chino, T. Tanaka, and T. Endo Synth. Commun. 26 1996 2145 2154
9. R.L. Funk, and K.P.C. Vollhardt J. Am. Chem. Soc. 98 1976 6755 6757
10. Palladium-catalyzed generation of an equivalent to oQDM and its reaction with ketones and imines have been recently reported; see: S. Ueno, M. Ohtsubo, and R. Kuwano Org. Lett. 12 2010 4332 4334
11. S. Ueno, M. Ohtsubo, and R. Kuwano J. Am. Chem. Soc. 131 2009 12904 12905
12. A.G. Griesbeck, and S. Stadtmüller Chem. Ber. 126 1993 2149 2150
13. S. Kamijo, T. Hoshikawa, and M. Inoue Tetrahedron Lett. 52 2011 2885 2888