Asymmetric synthesis of 3,4-dihydroxyglutamic acids via enantioselective reduction of cyclic meso-imide

Tetrahedron

Volumn 60, Issue 37, 2004, Pages 8089-8092

  Oba, Makoto ^a   Koguchi, Shinichi ^a   Nishiyama, Kozaburo ^a  

^a TOKAI UNIVERSITY   (Japan)

Author keywords

3,4 Dihydroxyglutamic acid; Asymmetric synthesis; Desymmetrization; meso Imide

Indexed keywords

GLUTAMIC ACID DERIVATIVE; IMIDE; LACTAM; LEWIS ACID; TARTARIC ACID DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CYANATION; DEPROTECTION REACTION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; REDUCTION; STANDARD; STEREOCHEMISTRY;

EID: 4143059339     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.109     Document Type: Article

References (18)

1. A.I. Virtanen, and T. Ettala Soumen Kemistilehti B29 1956 107 108
2. P. Dauban, C. De Saint-Fuscien, and R.H. Dodd Tetrahedron 55 1999 7589 7600
3. P. Dauban, C. De Saint-Fuscien, F. Acher, L. Prezeau, I. Brabet, J.-P. Pin, and R.H. Dodd Bioorg. Med. Chem. Lett. 10 2000 129 133
4. N. Langlois Tetrahedron Lett. 40 1999 8801 8803
5. M. Oba, S. Koguchi, and K. Nishiyama Tetrahedron Lett. 42 2001 5901 5902
6. M. Oba, S. Koguchi, and K. Nishiyama Tetrahedron 58 2002 9359 9363
7. M. Shimizu, Y. Nishigaki, and A. Wakabayashi Tetrahedron Lett. 40 1999 8873 8876
8. R. Romagnoli, E.C. Roos, H. Hiemstra, M.J. Moolenaar, and W.N. Speckamp Tetrahedron Lett. 35 1994 1087 1090
9. M. Ostendorf, R. Romagnoli, I.C. Pereiro, E.C. Roos, M.J. Moolenaar, W.N. Speckamp, and H. Hiemstra Tetrahedron: Asymmetry 8 1997 1773 1789
10. R.A. Dixon, and S. Jones Tetrahedron: Asymmetry 13 2002 1115 1119
11. K. Matsuki, H. Inoue, A. Ishida, M. Takeda, M. Nakagawa, and T. Hino Heterocycles 36 1993 937 940
12. K. Matsuki, H. Inoue, A. Ishida, M. Takeda, M. Nakagawa, and T. Hino Chem. Pharm. Bull. 42 1994 9 18
13. S.A. Miller, and A.R. Chamberlin J. Org. Chem. 54 1989 2502 2504
14. S.A. Miller, and A.R. Chamberlin J. Am. Chem. Soc. 112 1990 8100 8112
15. J. Kang, J.W. Lee, J.I. Kim, and C. Pyun Tetrahedron Lett. 36 1995 4265 4268
16. R. Noyori, I. Tomino, and Y. Tanimoto J. Am. Chem. Soc. 101 1979 3129 3131
17. R. Noyori, I. Tomino, Y. Tanimoto, and M. Nishizawa J. Am. Chem. Soc. 106 1984 6709 6716
18. 4,5 of the syn adduct is larger than that of the anti isomer. See Ref. 7.