Enantioselective titanium-catalyzed sulfides oxidation: Novel ligands provide significantly improved catalyst life

Journal of Organic Chemistry

Volumn 61, Issue 15, 1996, Pages 5175-5177

  Di Furia, Fulvio ^a   Licini, Giulia ^a   Modena, Giorgio ^a   Motterle, Riccardo ^a   Nugent, William A ^b  

^a UNIVERSITY OF PADOVA   (Italy)

^b DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000858607     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960359z     Document Type: Article

References (22)

1. Ojima, I. Catalytic Asymmetric Synthesis; VCH Publishers, Inc.: New York, 1993. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, Inc.: New York, 1994.
2. Ojima, I. Catalytic Asymmetric Synthesis; VCH Publishers, Inc.: New York, 1993. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, Inc.: New York, 1994.
3. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
4. Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325.
5. (a) Pitchen, P.; Dunach, E.; Deshmukh, M. N.; Kagan, H. B. J. Am. Chem. Soc. 1984, 106, 8188.
6. (b) Zhao, S. H.; Samuel, O.; Kagan, H. B. Tetrahedron 1987, 43, 5132. Brunel, J. M.; Diter, P.; Duetsch, M.; Kagan, H. B. J. Org. Chem. 1995, 60, 8086.
7. (b) Zhao, S. H.; Samuel, O.; Kagan, H. B. Tetrahedron 1987, 43, 5132. Brunel, J. M.; Diter, P.; Duetsch, M.; Kagan, H. B. J. Org. Chem. 1995, 60, 8086.
8. Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 4529.
9. 4b) could be employed by carrying out the oxidations in the presence of activated molecular sieves.
10. Conte, V.; Di Furia, F.; Licini, G.; Modena, G.; Sbampato, G. In Dioxygen Activation and Homogeneous Catalytic Oxidation; Simandi, L. I., Ed.; Elsevier Science Publishers B.V.: Amsterdam, The Netherlands, 1991; p 385.
11. Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 6142.
12. Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768.
13. 8,9
14. Part of this work has been presented at the COFEM Conference "Giornate di Chimica Fisica Organica e Meccanicistica", Perugia, Italy, September 24-27, 1995.
15. 2, 0°C, 91% yield): Boche, G.; Möbus, K.; Harms, K.; Marsh J. Am. Chem. Soc. 1996, 118, 2770.
16. 4 and (+)-1b in 1,2-dichloroethane at rt and removal of the solvent under vacuum.
17. Sugimoto, T.; Kokubo, T.; Miyazaki, J.; Tanimoto, S.; Okano, M. J. Chem. Soc., Chem. Commun. 1979, 402. Sakuraba, H.; Natori, K.; Tanaka, Y. J. Org. Chem. 1991, 56, 4124.
18. Sugimoto, T.; Kokubo, T.; Miyazaki, J.; Tanimoto, S.; Okano, M. J. Chem. Soc., Chem. Commun. 1979, 402. Sakuraba, H.; Natori, K.; Tanaka, Y. J. Org. Chem. 1991, 56, 4124.
19. In sulfoxide asymmetric synthesis both enantioselective oxidation and kinetic resolution have been contemporarily observed and also in other chiral metal-catalyzed processes. Cf. ref 5. Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 7624; Nagata, T.; Imagawa, K.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 3241.
20. In sulfoxide asymmetric synthesis both enantioselective oxidation and kinetic resolution have been contemporarily observed and also in other chiral metal-catalyzed processes. Cf. ref 5. Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 7624; Nagata, T.; Imagawa, K.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 3241.
21. Bonchio, M.; Campestrini, S.; Conte, V.; Di Furia, F.; Moro, S. Tetrahedron 1995, 51, 12363.
22. Bissing, D. E.; Matuszac, C. A.; McEwen, W. E. J. Am. Chem. Soc. 1964, 86, 3824.