Diastereoselective Photooxygenation of Chiral Naphthyl Alcohols: The Hydroxy Group Directing Effect in Singlet Oxygen [4 + 2] Cycloaddition to Arenes

Journal of the American Chemical Society

Volumn 117, Issue 25, 1995, Pages 6686-6690

  Adam, Waldemar ^a   Prein, Michael ^a   Peters, Eva Maria ^b   Peters, Karl ^b   von Schnering, Hans Georg ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001400709     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00130a006     Document Type: Article

References (26)

1. Fritzsche, M.C.R. Acad. Sci. 1867, 64, 1035.
2. Moureu, C.; Dufraisse, C.; Dean, P.M.C. Hebd. Sci. 1926, 182, 1440.
3. Schenck, G.O.; Ziegler, K. Naturwissenschaften 1944, 32, 157.
4. Clennan, E.L.; Foote, C.S. In Organic Peroxides; Ando, W., Ed.; Wiley & Sons: Chichester, 1992; Section 245.
5. Paquette, L.A. In Asymmetric Synthesis; Morrison, J.D., Ed.; Academic Press: New York, 1984; Chapter 7.
6. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876.
7. Ciganek, E. Org. React. (N.Y.) 1984, 32, 1.
8. Kahn, S.D.; Hehre, W.J. J. Am. Chem. Soc. 1987, 109, 663.
9. Brown, F.K.; Houk, K.N.; Burnell, D.J.; Valenta, Z. J. Org. Chem. 1987, 52, 3050.
10. Tripathy, R.; Franck, R.W.; Onan, K.D. J. Am. Chem. Soc. 1988, 110, 3257.
11. Fisher, M.J.; Hehre, W.J.; Kahn, S.D.; Overman, L.E. J. Am. Chem. Soc. 1988, 110, 4625.
12. Ishida, M.; Beniya, Y.; Inagaki, S.; Kato, S. J. Am. Chem. Soc. 1990, 112, 8980.
13. Macaulay, J.B.; Fallis, A.G. J. Am. Chem. Soc. 1990, 112, 1136.
14. Coxon, J.M.; McDonald, D.Q. Tetrahedron Lett. 1992, 33, 651.
15. Ishida, M.; Aoyama, T.; Beniya, Y.; Yamabe, S.; Kato, S.; Inagaki, S. Bull. Chem. Soc. Jpn. 1993, 66, 3430.
16. Adam, W.; Nestler, B. J. Am. Chem. Soc. 1992, 114, 6549.
17. Adam, W.; Briinker, H.-G. J. Am. Chem. Soc. 1993, 115, 3008.
18. Adam, W.; Prein, M. J. Am. Chem. Soc. 1993, 115, 3766.
19. Prein, M.; Adam, W.; Maurer, M.; Peters, E.M.; Peters, K.; von Schnering, H.G. Chem. Eur. J. 1995, 1, 89.
20. Adam, W.; Prein, M. Tetrahedron Lett. 1994, 35, 4331.
21. Wasserman, H.H.; Larsen, D.L. J. Chem. Soc., Chem. Commun. 1972, 253.
22. van den Heuvel, C.J.M.; Steinberg, H.; de Boer, Th. J. Recl.: J.R. Neth. Chem. Soc. 1980, 99, 109.
23. Gollnick, K.; Kuhn, H.J. In Singlet Oxygen; Wasserman, H.H., Murray, R.W., Eds.; Academic Press: New York, 1979.
24. Gorman, A.A.; Hamblett, I.; Lambert, C.; Spencer, B.; Standen, M.C. J. Am. Chem. Soc. 1988, 110, 8053.
25. Clennan, E.L. Tetrahedron 1991, 47, 1343.
26. Broeker, J.L.; Hoffmann, R.W.; Houk, K.N. J. Am. Chem. Soc. 1991, 113, 5006.