Stereoselective photooxidation of enecarbamates: Reactivity of ozone vs singlet oxygen

Organic Letters

Volumn 7, Issue 11, 2005, Pages 2089-2092

  Sivaguru, J ^a   Saito, Hideaki ^a,b   Poon, Thomas ^c   Omonuwa, Toma ^a   Franz, Roberto ^a   Jockusch, Steffen ^a   Hooper, Catherine ^c   Inoue, Yoshihisa ^b   Adam, Waldemar ^d,e   Turro, Nicholas J ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b KECK GRADUATE INSTITUTE   (United States)

^c OSAKA UNIVERSITY   (Japan)

^d UNIVERSITY OF WÜRZBURG   (Germany)

^e UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; OXAZOLIDINONE DERIVATIVE; OXYGEN; OZONE;

ARTICLE; CHEMICAL REACTION; OXIDATION; PHOTOOXIDATION; STEREOCHEMISTRY; VIBRATION;

EID: 20644442451     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0502230     Document Type: Article

References (30)

1. (a) Taylor, M. S.; Jacobsen, E. N. Proc. Natl. Acad. Sci. 2004, 101, 5368-5373.
2. (b) Evans, D. A. In Asymmetric Synthesis. Stereodifferentiating Reactions; Morrison, J. D., Ed.; Academic Press: New York; 1984; Vol. 3, Part B, p 1.
3. (c) Ojima, I. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; Jai Press, Inc.: Greenwich, CT, 1995; p 95.
4. (a) Inoue, Y.; Ramamurthy, V. Chiral Photochemistry; Marcel Dekker: New York, 2004.
5. (b) Lewis, T. J.; Randall, L. H.; Rettig, S. J.; Scheffer, J. R.; Trotter, J.; Wu, C.-H. J. Am. Chem. Soc. 1996, 118, 6167.
6. (c) Leibovitch, M.; Olovsson, G.; Sundarababu, G.; Ramamurthy, V.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1996, 118, 1219.
7. (d) Chong, K. C. W.; Sivaguru, J.; Shichi, T.; Yoshimi, Y.; Ramamurthy, V.; Scheffer, J. R. J. Am. Chem. Soc. 2002, 124, 2858-2859.
8. Poon, T.; Sivaguru, J.; Franz, R.; Jockusch, S.; Martinez, C.; Washington, I.; Adam, W.; Inoue, Y.; Turro, N. J. J. Am. Chem. Soc. 2004, 126, 10498-10499.
9. Sivaguru, J.; Poon, T.; Franz, R.; Jockusch, S.; Adam, W.; Turro, N. J. J. Am. Chem. Soc. 2004, 126, 10816-10817.
10. (a) Wasserman, H. H.; Murray, R. W., Eds.; Singlet Oxygen; Academic: New York; 1979.
11. (b) Frimer, A. A., Ed. Singlet Oxygen; CRC: Boca Raton; 1985; Vols. 1-4.
12. (c) Gollnick, K.; Kuhn, H. J. Singlet Oxygen; Wasserman, H. H.; Murray, R. W.; Eds.; Academic: New York, 1979.
13. (d) Foote, C. S. Acc. Chem. Res. 1968, 1, 104.
14. (e) Gollnik, K. Adv. Chem. 1968, 77, 78.
15. Bailey, P. S. Ozonation in Organic Chemistry; New York, 1978; Vols. 1 and 2.
16. (a) Wadt, W. R.; Goddard, W. A., III. J. Am. Chem. Soc. 1975, 97, 3004-3021.
17. (b) Goddard, W. A., III; Dunning, T. J., Jr.; Hunt, W. J.; Hay, P. J. Acc. Chem. Res. 1973, 6, 368-376.
18. (a) Inoue, Y. Chem. Rev. 1992, 92, 741-70.
19. (b) Buschmann, H.; Scharf, H.-D.; Hoffmann, N.; Esser, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 477-515.
20. (c) Otera, J.; Sakamoto, K.; Tsukamoto, T.; Orita, A. Tetrahedron Lett. 1998, 39, 3201.
21. Leffler, J. E. J. Org. Chem. 1955, 20, 1202.
22. (a) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5-26.
23. (b) Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330.
24. (c) Martin, V. S.; Woodward, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237.
25. (d) Ching, S. C.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104 (25), 7294-7299.
26. Structure of the (Z)-isomer was obtained by crystallography; see: Adam, W.; Bosio, S. G.; Turro, N. J.; Wolff, B. T. J. Org. Chem. 2004, 69, 1704.
27. Poon, T.; Turro, N. J.; Chapman, J.; Lakshminarasimhan, P.; Lei, X.; Jockusch, S.; Franz, R.; Washington, I.; Adam, W.; Bosio, S. G. Org. Lett. 2003, 5, 4951-4953.
28. (a) Mori, A.; Abe, M.; Nojima, M. J. Org. Chem. 2001, 66, 3548.
29. (b) Stephenson, L. M.; Zielinski, M. B. J. Am. Chem. Soc. 1982, 104, 5819.
30. 2, while at lower temperatures, the ozonide itself is an oxidant (ref 13a).