Oxidation of functional olefines : Synthesis of protected amino acids bearing a terminal α-hydroxyketo group

Tetrahedron Letters

Volumn 37, Issue 19, 1996, Pages 3333-3334

  David, Katerine ^a   Greiner, Alfred ^b   Goré, Jacques ^a   Cazes, Bernard ^a  

^a UNIVERSITÉ LYON 1   (France)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029925755     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00570-9     Document Type: Article

References (17)

1. Ohfune, Y. Acc. Chem. Res. 1992, 25, 360-366 and references cited therein.
2. Kanazawa, K. ; Tsuchiya, K. ; Araki, T. Am. Rev. Respirat. Diseases, 1960, 81, 924.
3. Miyake, A. Chem. Pharm. Bull. 1960, 8, 1071-1073 and Chem. Pharm. Bull. 1960, 8, 1079-1083.
4. Miyake, A. Chem. Pharm. Bull. 1960, 8, 1071-1073 and Chem. Pharm. Bull. 1960, 8, 1079-1083.
5. Yamaguchi, M. ; Yamaki, H. ; Shinoda, T. ; Tago, Y. ; Suzuki, H. ; Nishimura, T. ; Yamagushi, H. J. Antibiot. 1990, 43, 411-416.
6. a) Miyake, A. Chem. Pharm. Bull. 1960, 8, 1074-1078.
7. b) Mooiweer, H.H.; Ettema, K.W.A.; Hiemstra, H.; Speckamp, W.N. Tetrahedron 1990, 46, 2991-2998.
8. a) Schmidt, U.; Stäbler, F.; Lieberknecht, A. Synthesis 1992, 482-486.
9. b) Jackson, R.F.W.; Wishart, N.; Wood, A.; James, K.; Wythes, M.J. J. Org. Chem. 1992, 57, 3397-3404.
10. c) Baldwin, J.E.; Adlington, R.M.; Godfrey, C.R.A.; Gollins, D.W.; Smith, M.L.; Russel, A.T. Synlett 1993, 51-53.
11. Leanna, M.R.; Morton, H.E. Tetrahedron Lett. 1993, 34, 4485-4488.
12. e) Goluber, A.; Sewwald, N.; Burger, K. Tetrahedron Lett. 1993, 34, 5879-5880.
13. Murahashi, S.I. ; Saito, T. ; Hanaoka, H. ; Mutakami, Y. ; Naota, T. ; Kumobayashi, H. ; Akutagawa, S. J. Org. Chem. 1993, 58, 2929-2930.
14. Murahashi, S.I. ; Naota, T. ; Hanaoka, H. Chem. Lett. 1993, 43, 1767-1770.
15. Amines and amides are known to be oxidized under the reaction conditions : Murahashi, S.I. ; Saito, T. ; Naota, T. ; Kumobayashi, H. ; Akutagawa, S. Tetrahedron Lett. 1991, 32, 2145-2148.
16. These protected aminomalonates (1-5)b-c were obtained through the alkylation of diethyl acetamidomalonate and N-Boc-aminomalonate; decarboxylation of acetamidomalonates (2-5)b led classically to acetamidoesters (2-5)a.
17. 3, 200 MHz) δ ppm : 1.25 (6H, t, J=7.1 Hz) ; 1.36 (6H, s) ; 1.40 (9H, s) ; 3.56 (OH, broad s) ; 3.78 (2H, s); 4.07-4.35 (4H, m) ; 6.15 (NH, broad s).