New chiral alanine template with a 1,2,3,6-tetrahydro-2-pyrazinone structure for the asymmetric synthesis of α-methyl α-amino acids

Tetrahedron Asymmetry

Volumn 9, Issue 13, 1998, Pages 2211-2214

  Abellán, Tomás ^a   Nájera, Carmen ^a   Sansano, José M ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

6 ISOPROPYL 5 PHENYL 1,2,3,6 TETRAHYDRO 2 PYRAZINONE; ALANINE; PALLADIUM; PYRAZINE DERIVATIVE; UNCLASSIFIED DRUG; VALINE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG HYDROLYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0345337272     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00208-0     Document Type: Article

References (16)

1. (a) Wirth, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
2. (b) Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243-2266.
3. (a) Williams, R. M. In Synthesis of Optically Active Amino Acids, Pergamon Press: Oxford, 1989.
4. (b) Duthaler, R. O. Tetrahedron 1994, 50, 1540-1650.
5. (c) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748.
6. (d) Alonso, F.; Davies, S. G.; Elend, A. S.; Haggitt, J. L. J. Chem. Soc., Perkin Trans. 1 1998, 257-264.
7. Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Angew. Chem. Int. Ed. Engl. 1997, 36, 995-997.
8. Studer, A.; Seebach, D. Liebigs Ann. Chem. 1995, 217-222.
9. To our knowledge the only example of this type of heterocycle is 1,2,3,6-tetrahydro-6,6-dimethyl-5-phenylpyrazinone, which has been prepared by reaction of 2,2-dimethyl-3-phenyl-2H-azirine with glycine ethyl ester: Alvernhe, G.; Laurent, A.; Masroua, A. Tetrahedron Lett. 1983, 24, 1153-1156.
10. 3.
11. 1H NMR (300 MHz).
12. The chemical shifts for the methyl groups at 3-position of the trans and cis diastereomers (1.72 and 1.65, respectively) are similar to those observed in the oxazinones (1.74 and 1.70, respectively).
13. PC Model for Windows from Serena Software and Hyperchem 5.0 from Hypercube were used for these calculations.
14. Cativiela, C.; Díaz-de Villegas, M. D.; Gálvez, J. A. Tetrahedron: Asymmetry 1994, 5, 261-268.
15. Dictionary of Organic Compounds, Chapman and Hall: New York, 1982.
16. We have already communicated the preparation of α,β-didehydro α-amino acid derivatives by means of the corresponding glycine equivalent: First International Electronic Conference on Synthetic Organic Chemistry (ECSOC-1), A0007, September 1997.