Catalytic enantioselective oxidation of alkanes and alkenes using (salen)manganese complexes bearing a chiral binaphthyl strapping unit

Advanced Synthesis and Catalysis

Volumn 346, Issue 2-3, 2004, Pages 195-198

  Murahashi, Shun Ichi ^a,b   Noji, Satoru ^b   Komiya, Naruyoshi ^b  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

Asymmetric epoxidation; Asymmetric hydroxylation; C H activation; Hydrocarbons; Iodosylbenzene; Salen manganese complex

Indexed keywords

ALKANE; ALKENE; MANGANESE DERIVATIVE; NAPHTHYL GROUP;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; EPOXIDATION; HYDROXYLATION; OXIDATION KINETICS;

EID: 1942535125     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303190     Document Type: Article

References (24)

1. Comprehensive Asymmetric Catalysts, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999.
2. a) J. T. Groves, P. Viski, J. Am. Chem. Soc. 1989, 111, 8537-8538;
3. b) J. T. Groves, P. Viski, J. Org. Chem. 1990, 55, 3628-3634.
4. R. Zhang, W.-Y. Yu, T.-S. Lai, C.-M. Che, Chem. Commun. 1999, 1791-1792.
5. a) T. Hamada, R. Irie, J. Mihara, K. Hamachi, T. Katsuki, Tetrahedron. 1998, 54, 10017-10028;
6. b) K. Hamachi, R. Irie, T. Katsuki, Tetrahedron Lett. 1996, 37, 4979-4982.
7. a) W. Zhang, J. L. Loebach, S. R. Wilson, E. N. Jacobsen, J. Am. Chem. Soc. 1990, 112, 2801-2803;
8. For review, see: b) E. N. Jacobsen, in: Catalytic Asymmetric Synthesis, (Ed.: I. Ojima), VCH, Weinheim, 1993, pp. 159-202.
9. For reviews, see: a) T. Katsuki, Synlett 2003, 281-297; b) Y. N. Ito, T. Katsuki, Bull. Chem. Soc. Jpn. 1999, 72, 603-619; c) T. Katsuki, J. Mol. Catal. A: Chem. 1996, 113, 87-107; d) T. Katsuki, Coord. Chem. Rev. 1995, 140, 189-214.
10. For reviews, see: a) T. Katsuki, Synlett 2003, 281-297; b) Y. N. Ito, T. Katsuki, Bull. Chem. Soc. Jpn. 1999, 72, 603-619; c) T. Katsuki, J. Mol. Catal. A: Chem. 1996, 113, 87-107; d) T. Katsuki, Coord. Chem. Rev. 1995, 140, 189-214.
11. For reviews, see: a) T. Katsuki, Synlett 2003, 281-297; b) Y. N. Ito, T. Katsuki, Bull. Chem. Soc. Jpn. 1999, 72, 603-619; c) T. Katsuki, J. Mol. Catal. A: Chem. 1996, 113, 87-107; d) T. Katsuki, Coord. Chem. Rev. 1995, 140, 189-214.
12. For reviews, see: a) T. Katsuki, Synlett 2003, 281-297; b) Y. N. Ito, T. Katsuki, Bull. Chem. Soc. Jpn. 1999, 72, 603-619; c) T. Katsuki, J. Mol. Catal. A: Chem. 1996, 113, 87-107; d) T. Katsuki, Coord. Chem. Rev. 1995, 140, 189-214.
13. For reviews, see: a) S.-I. Murahashi, Angew. Chem. Int. Ed. Engl. 1995, 34, 2443-2465; b) S.-I. Murahashi, N. Komiya, In: Biomimetic Oxidations Catalyzed by Transition Metal Complexes, (Ed.: B. Meunier), Imperial College Press: London, 2000, pp. 563-611.
14. For reviews, see: a) S.-I. Murahashi, Angew. Chem. Int. Ed. Engl. 1995, 34, 2443-2465; b) S.-I. Murahashi, N. Komiya, In: Biomimetic Oxidations Catalyzed by Transition Metal Complexes, (Ed.: B. Meunier), Imperial College Press: London, 2000, pp. 563-611.
15. a) S.-I. Murahashi, Y. Oda, T. Naota, J. Am. Chem. Soc. 1992, 114, 7913-7914;
16. b) N. Komiya, T. Naota, Y. Oda, S.-I. Murahashi, J. Mol. Catal. A: Chem. 1997, 117, 21-37;
17. c) S.-I. Murahashi, N. Komiya, Y. Oda, T. Kuwabara, T. Naota, J. Org, Chem. 2000, 65, 9186-9193.
18. N. Komiya, S. Noji, S.-I. Murahashi, Tetrahedron Lett. 1998, 39, 7921-7924.
19. th Annual Meeting of Chemical Society of Japan (Chiba) 2000, Abstr. 4F402.
20. M. D. Kaufman, P. A. Grieco, D. W. Bougie, J. Am. Chem. Soc. 1993, 115, 11648-11649.
21. N. S. Finney, P. J. Pospisil, S. Chang, M. Palucki, R. G. Konsler, K. B. Hansen, E. N. Jacobsen, Angew. Chem. Int. Ed. Engl. 1997, 36, 1720-1723.
22. Enantiomeric excess was determined by HPLC analysis using CHIRALPAK AD (hexane:2-propanol = 10:1).
23. 3. cis/trans epoxide ratio was 3.5:1.
24. T. Hashihayata, Y. Ito, T. Katsuki, Tetrahedron 1997, 53, 9541-9552.