Diureas as ligands in asymmetric reduction of ketones

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5196-5197

  Gamez, Patrick ^a   Dunjic, Branko ^a   Lemaire, Marc ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041362890     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960574f     Document Type: Article

References (24)

1. (a) Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 1123.
2. (b) Sharpless, K. B. J. Org. Chem. 1992, 57, 5067.
3. (a) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063.
4. (b) Jacobsen, E. N. J. Org. Chem. 1993, 58, 6939.
5. (c) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378.
6. (a) Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
7. (b) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566.
8. (c) Zhou, Q. L.; Pfaltz, A. Tetrahedron 1994, 50, 4467.
9. (d) Pfaltz, A.; von Matt, P.; Lloyd-Jones, C.; Minidis, A. B. E. Helv. Chim. Acta 1995, 78, 265.
10. (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562.
11. (b) Ohkuma, T.; Ooka, H.; Ikariya, T; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417.
12. Nagata, T.; Yorozu, K.; Yamada, T.; Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2145.
13. (a) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897.
14. (b) Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705.
15. (c) Gamez, P.; Dunjic, B.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 1109.
16. (a) Botteghi, C.; Chelucci, G.; Chessa, G.; Delogu, G.; Gladiali, S.; Soccolini, F. J. Organomet. Chem. 1986, 304, 217.
17. (b) Gladiali, S.; Chelucci, G.; Chessa, G.; Delogu, G.; Soccolini, F. J. Organomet. Chem. 1987, 327, C15.
18. (c) Gladiali, S.; Chelucci, G.; Soccolini, F.; Delogu, G.; Chessa, G. J. Organomet. Chem. 1989, 370, 285.
19. (d) Gladiali, S.; Pinna, L.; Delogu, G.; De Martin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635.
20. Gamez, P.; Dunjic, B.; Fache, F.; Lemaire, M. J. Chem. Soc., Chem. Commun. 1994, 1417.
21. Urea Synthesis. Typical procedure is described in the supporting information.
22. Hydride Transfer Reduction. Typical procedure is described in the supporting information.
23. Mc Leod, R.; Welch, F. J.; Mosher, H. S. J. Am. Chem. Soc. 1960, 82, 876-880.
24. N,N′-Dimethyl-1,2-diphenylethanediamine (2) was synthesized according to: Mangeney, P.; Tejero, T.; Alexakis, A.; Normant, J. F. Synthesis 1988, 255.