Remarkable reversal of the non-linear effect in the catalytic enantioselective allylic oxidation of cyclohexene using copper proline complexes and t-butyl hydroperoxide

Tetrahedron Asymmetry

Volumn 7, Issue 7, 1996, Pages 1895-1898

  Zondervan, Charon ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXENE DERIVATIVE;

ARTICLE; CHIRALITY; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030200570     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00224-8     Document Type: Article

References (22)

1. 1 Jacobsen, E. N.Asymmetric Epoxidation of Unfunctionalized Olefins. In Catalytic Asymmetric Synthesis, Ojima, I. Ed.; VCH: New York, 1993, 159-202.
2. 2 (a) Katsuki, T.; Sharpless, K.B. J. Am. Chem. Soc. 1980, 102, 5974;
3. (b) Johnson, R. A.; Sharpless, K. B. Catalytic Asymmetric Epoxidation of Allylic Alcohols. In Catalytic Asymmetric Synthesis, Ojima, I. Ed.; VCH: New York, 1993, 103-158.
4. 3 Johnson, R. A.; Sharpless, K. B. Catalytic Asymmetric Dihydroxylation. In Catalytic Asymmetric Synthesis, Ojima, I. Ed.; VCH: New York, 1993, 227-272.
5. 4 (a) Muzart, J. J. Mol. Catal. 1991, 64, 381;
6. (b) Patent 2,625,030, 1976, Sumitomo Chemical Co.; C.A. 1977, 86, 120886.
7. 5 (a) Rispens, M. T.; Zondervan, C.; Feringa, B. L. Tetrahedron: Asym. 1995, 6, 661;
8. (b) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831;
9. (c) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945;
10. (d) Levina, A.; Muzart, J. Tetrahedron: Asym. 1995, 6, 147.
11. 6 Shul'pin, G. B.; Bochkova, M. M.; Nizova, G. V. J. Chem. Soc., Perkin Trans 2, 1995, 1465.
12. 7 Hansson, S.; Heumann, A.; Rein, T.; Åkermark, B. J. Org. Chem. 1990, 55, 975.
13. 8 Preparation of these compounds according to: Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390.
14. 9 (a) Wijnberg, H.; Feringa, B.L. Tetrahedron 1976, 32, 2831;
15. (b) Guillaneux, D.; Zhao, S.-H.; Samuel, O.; Rainford, D.; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430;
16. (c) Tanaka, K.; Matsui, J.; Kawabata, Y.; Suzuki, H.; Watanabe, A. J. Chem. Soc., Chem. Commun. 1994, 1632.
17. (d) Kagan, H.B.; Puchot, C.; Samuel, O.; Dunach, E.; Zhao, S.; Agami, C. J. Am. Chem. Soc. 1986, 108, 2352.
18. 10 Structurally characterized bis(aquo)-bis(S)prolinato copper(II) contains two chiral ligands. This complex gave the same results compared to the 'in situ' prepared catalyst. For the X-ray structure see: Mathieson, A. McL.; Welsh, H.K. Acta Cryst. 1952, 5, 599.
19. 11 Beckwith, A. L. J.; Zavitsas, A. A. J. Am. Chem. Soc. 1986, 108, 8230.
20. 12 Levina, A.; Hénin, F.; Muzart, J. J. Organomet. Chem. .1995, 494, 165.
21. 13 Overman, L. E. Angew. Chem. Int. Ed. Engl. 1984, 23, 579.
22. 2 system in allylic acetoxylation of olefins see Jia, C.; Muller, P.; Mimoun, H. J. Mol. Catal. A: Chemical 1995,101, 127.