Enantioselective synthesis of β-amino acids. 7. Preparation of enantiopure α-substituted β-amino acids from 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one

Tetrahedron Asymmetry

Volumn 7, Issue 8, 1996, Pages 2233-2246

  Juaristi, Eusebio ^a   Quintana, Delia ^a   Balderas, Margarita ^a   García Pérez, Enrique ^a  

^a DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINO ACID;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030220984     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00278-9     Document Type: Article

References (28)

1. 1. For part 6, see: Escalante, J.; Juaristi, E. Tetrahedron Lett. 1995, 36, 4397.
2. 2. A preliminary report of this work was published: Juaristi, E.; Quintana, D. Tetrahedron: Asymmetry 1992, 3, 723.
3. 3. See, for example: (a) Spatola, A.F. In Chemistry and Biochemistry of Amino Acids, Peptides and Proteins; Weinstein, B. (Ed.) Marcel Dekker: New York, 1983; Vol. 7, pp 331-333.
4. (b) Drey, C.N.C. In Chemistry and Biochemistry of Amino Acids; Barrett, G.C. (Ed.) Chapman and Hall: London, 1985.
5. 4. See, for example: (a) Georg, G.I. (Ed.) Organic Chemistry of β-Lactams. VCH Publishers: New York, 1992.
6. (b) Page, M.I. (Ed.) The Chemistry of β-Lactams, Chapman and Hall: London, 1992.
7. 5. Juaristi, E.; Quintana, D.; Escalante, J. Aldrichimica Acta 1994, 27, 3.
8. (b) Cole, D.C. Tetrahedron 1994, 50, 9517.
9. (c) Juaristi, E. (Ed.) Enantioselective Synthesis of β-Amino Acids, VCH Publishers: New York, in press.
10. 6. Juaristi, E.; Quintana, D.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1991, 56, 2553.
11. 1,3 strain: Seebach, D.; Lamatsch, B.; Amstutz, R.; Beck, A.K.; Dobler, M.; Egli, M.; Fitzi, R.; Gautschi, M.; Herradón, B.; Hidber, P.C.; Irwin, J.J.; Locher, R.; Maestro, M.; Maetzke, T.; Mouriño, A.; Pfammatter, E.; Plattner, D.A.; Schickli, C.; Schweizer, W.B.; Seiler, P.; Stucky, G.; Petter, W.; Escalante, J.; Juaristi, E.; Quintana, D.; Miravitlles, C.; Molins, E. Helv. Chim. Acta 1992, 75, 913.
12. 8. Limited amounts of both enantiomers of 1 became first available via preparative resolution by recycling chromatography on chiraspher. Kinkel, J.; Gysel, U.; Blaser, D.; Seebach, D. Helv. Chim. Acta 1991, 74, 1622. We are grateful to these researchers for a sample of the resolved material.
13. 9. (a) Fitzi, R.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1986, 25, 345.
14. (b) See, also: Fitzi, R.; Seebach, D. Tetrahedron 1988, 44, 5277.
15. 10. Juaristi, E.; Rizo, B.; Natal, V.; Escalante, J.; Regla, I. Tetrahedron: Asymmetry 1991, 2, 821.
16. 11. (a) Chu, K.S.; Negrete, G.R.; Konopelski, J.P.; Lakner, F.J.; Woo, N.-T.; Olmstead, M.M. J. Am. Chem. Soc. 1992, 114, 1800.
17. (b) See also: Hardy, P.M.; Samworth, D.J. J. Chem. Soc., Perkin Trans. 1 1977, 1954.
18. 12. The 98% overall yield for these two steps reported in reference 2 is in error.
19. 13. McMurry, J.E.; Blaszczack, L.C. J. Org. Chem. 1974, 39, 2217.
20. 14. Alternatively, decarboxylation can be achieved by electrolysis: (a) Lakner, F.J.; Chu, K.S.; Negrete, G.R.; Konopelski, J.P. Org. Synth. 1995, 73, 201.
21. (b) See, also: Seebach, D.; Charczuk, R.; Gerber, C.; Renaud, P.; Berner, H.; Schneider, H. Helv. Chim. Acta 1989, 72, 401.
22. (c) Lamatsch, B.; Quintana, D. Unpublished results.
23. 15. The absolute configuration of (-)-α-methyl-β-alanine is known: Balenovic, K.; Bregant, N. Tetrahedron 1959, 5, 44.
24. 16. Further confirmation of the absolute configuration in (+)-1 comes from the X-ray crystallographic structure of cis-12: Molins, E. Unpublished observations.
25. 17. Specific rotations and physical and spectroscopic properties of the free amino acids are usually sensitive to conditions of measurement; see, for example: Juaristi, E.; Escalante, J.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1992, 57, 2396.
26. 18. Brown, H.C.; Kramer, G.W.; Levy, A.B.; Midland, M.M. Organic Synthesis via Boranes; Wiley: New York, 1975; p 256.
27. 19. Juaristi, E.; Martínez-Richa, A.; García-Rivera, A.; Cruz-Sánchez, J.S. J. Org. Chem. 1983, 48, 2603.
28. 20. Still, W.C.; Kahn, M.; Mitra, A., J. Org. Chem. 1978, 43, 2923.