Synthesis of enantiopure o-hydroxybenzylamines by stereoselective reduction of 2-imidoylphenols: Application in the catalytic enantioselective addition of diethylzinc to aldehydes

European Journal of Organic Chemistry

Volumn , Issue 4, 1999, Pages 805-811

  Palmieri, Gianni ^a  

^a Dipartimento di Scienze Chimiche dell'Universita   (Italy)

Author keywords

Aminophenols; Asymmetric synthesis; C C coupling; Conformation analysis; Reductions

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; BENZYLAMINE DERIVATIVE; PHENOL DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CATALYST; ENANTIOMER; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032856659     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199904)1999:4<805::aid-ejoc805>3.0.co;2-r     Document Type: Article

References (33)

1. [1a] R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69.
2. [1a] R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69.
3. [1b] K. Soai, S. Niwa, Chem. Rev. 1992, 92, 833-856.
4. [1c] R. Noyori, in Asymmetric Catalysis in Organic Synthesis, John Wiley: New York, 1994.
5. [1d] P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117-2188.
6. [1e] T. Mukaiyama, K. Soai, H. Shimizu, K. Suzuki, J. Am. Chem. Soc. 1979, 101, 1455.
7. [1f] M. Ognuni, T. Omi, Tetrahedron Lett. 1984, 25, 2823-2824.
8. [1g] R. Noyori, M. Kitamura, in Modern Synthetic Methods; (Ed.: R. Scheffold); Springer-Verlag, 1989; pp. 115-198.
9. [1h] P. Knochel, in Comprehensive Organic Synthesis; (Ed.: B. M. Trost); Pergamon Press, 1991; pp. 211-229.
10. [2a] G. Bartoli, M. Bosco, C. Cimarelli, R. Dalpozzo, G. De Munno, G. Palmieri, Tetrahedron: Asymmetry 1993, 4, 1651-1665.
11. [2b] C. Cimarelli, G. Palmieri, Tetrahedron 1998, 54, 15711-15720.
12. The o-pivaloylphenol, which is not commercially available, was prepared as described in: J. A. Miller, J. Org. Chem. 1987, 52, 322-323.
13. [4a] S. Boatman, C. R. Hauser, J. Org. Chem. 1966, 31, 1785-1789.
14. [4b] R. V. Singh, J. P. Tandon, J. Prakt. Chem. 1979, 321, 151.
15. [4c] P. G. Baraldi, D. Simoni, S. Manfredini, Synthesis 1983, 902-903.
16. [5a] G. Palmieri, C. Cimarelli, J. Org. Chem. 1996, 61, 5557-5563.
17. [5b] G.W. Gribble, C. F. Nutaitis, Org. Prep. Proced. Int. 1985, 17, 317-384.
18. [5c]D. A. Evans, K. T. Chapman, E. M. Carreira, J. Am. Chem. Soc. 1988, 110, 3560-3578.
19. [5d] D. Xu, K. Prasad, O. Repic, T. J. Blacklock, Tetrahedron: Asymmetry 1997, 8, 1445-1451.
20. [6a] J. L. Luche, J. Am. Chem. Soc. 1978, 100, 2226-2227.
21. [6b] A. L. Gemal, J. L. Luche, J. Am. Chem. Soc. 1981, 103, 5454-5459.
22. [7a] H. C. Brown, S. Krishnamurthy, Tetrahedron 1979, 35, 567-607.
23. [7b] R. G. Pearson, J. Am. Chem. Soc. 1963, 85, 3533-3539.
24. [8a] K. Neuvonen, K. Pihlaja, Magn. Reson. Chem. 1990, 28, 239-245.
25. [8b] K. Neuvonen, K. Pihlaja, J. Chem. Soc., Perkin Trans. II 1988, 461-467.
26. E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds; John Wiley: New York, 1994; pp. 646, 717, 718.
27. Semiempirical PM3 calculations were performed with the Spartan 5.0.3 program, Wavefunction, Inc., 18401 Von Karmen Ave., #370, Irvine, CA 92715.
28. [11a] I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, J. Am. Chem. Soc. 1991, 113, 4092-4096.
29. [11b] J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519.
30. Optical purities (% e.e.) were determined by GC analyses of the resulting alcohols on a chiral capillary column MEGADEX DMP β (30% dimethylpentyl-β-cyclodextrin on OV1701, 25 m, 0.25 mm ID, 0.25 μm film).
31. [13a] M. Kitamura, S. Suga, K. Kawai, R. Noyori, J. Am. Chem. Soc. I 1986, 108, 6071-6072.
32. [13b] J K. Mori, H. Norni, T. Chuman, M. Kohno, K. Kato, M. Noguchi, Tetrahedron 1982, 38, 3705-3711.
33. [13c] M. Watanabe, S. Araki, Y. Butsugan, M. Uemura, J. Org. Chem. 1991, 56, 2218-2224.