Catalytic asymmetric and chemoselective aerobic oxidation: Kinetic resolution of sec-alcohols

Tetrahedron Letters

Volumn 41, Issue 26, 2000, Pages 5119-5123

  Masutani, Kouta ^a   Uchida, Tatsuya ^a   Irie, Ryo ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Aerobic oxidation; Kinetic resolution; Ru salen complex

Indexed keywords

2 BUTANOL; ALCOHOL DERIVATIVE; BENZYLIDENEACETONE; HALOGEN; NITROSO DERIVATIVE; RUTHENIUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; ENANTIOMER; IRRADIATION; OPTICAL ROTATION; OXIDATION; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 0034709670     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00787-5     Document Type: Article

References (24)

1. (a) Comprehensive Organic Synthesis; Ley, S. V., Ed.; Pergamon Press: Oxford, 1991; Vol. 7.
2. (b) Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2.
3. (c) Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 2.
4. (a) Nagata, T.; Imagawa, K.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 1455-1465.
5. (b) Yamada, T.; Imagawa, K.; Nagata, T.; Mukaiyama, T. Chem. Lett. 1992, 2231-2234.
6. Bolm, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 1848-1849.
7. Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790-5792.
8. Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583-1584.
9. Hosokawa, T.; Okuda, C.; Murahashi, S. J. Org. Chem. 1985, 50, 1282-1287.
10. (a) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S. J. Org. Chem. 1999, 64, 2264-2271.
11. (b) idem. Tetrahedron Lett. 1995, 36, 9519-9520.
12. (a) Döbler, C.; Mehltreter, G.; Beller, M. Angew. Chem., Int. Ed. 1999, 38, 3026-3028.
13. (b) Krief, A.; Colaux-Castillo, C. Tetrahedron Lett. 1999, 40, 4189-4192.
14. Takeda, T.; Irie, R.; Katsuki, T. Synlett 1999, 1157-1159.
15. Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett. 1989, 30, 6545-6548.
16. Mn-Salen catalyzed oxidation of allylic alcohols has been reported to give epoxy alcohols: Adam, W.; Stegmann, V. R.; Saha-Möller, C. R. J. Am. Chem. Soc. 1999, 121, 1879-1882.
17. Allylic alcohols are oxidized to the corresponding carbonyl compounds by Cr-salen complex in the presence of iodosylbenzene: Adam, W.; Gelarcha, F. G.; Saha-Möller, C. R.; Stegmann, V. R. J. Org. Chem. 2000, 65, 1915-1918.
18. For the preparation of chiral (nitroso)(salen)ruthenium(II) chlorides, see: Uchida, T.; Irie, R.; Katsuki, T. Synlett 1999, 1163-1165 and Ref. 9.
19. (a) Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 13529-13530.
20. (b) Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738-8739.
21. (c) Kim, Y. H.; Park, D. H.; Byun, I. S. J. Org. Chem. 1998, 58, 4511-4512.
22. Ito, Y. N.; Katsuki, T. Bull. Chem. Soc. Jpn. 1999, 72, 603-619.
23. Hamada, T.; Fukuda, T.; Imanishi, H.; Katsuki, T. Tetrahedron 1996, 52, 515-530.
24. The OH-oxidation under irradiation of fluorescent light was four times faster than the reaction under irradiation of incandescent light.