Enantioselective synthesis of β-amino acids. Part 9: Preparation of enantiopure α,α-disubstituted β-amino acids from 1-benzoyl-2(S)-tert- butyl-3-methylperhydropyrimidin-4-one

Tetrahedron Asymmetry

Volumn 9, Issue 21, 1998, Pages 3881-3888

  Juaristi, Eusebio ^a   Balderas, Margarita ^a   Ramírez Quirós, Yara ^a  

^a DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARAGINE; BETA AMINO ACID; PYRIMIDINONE DERIVATIVE;

ALKYLATION; AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; HYDROLYSIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032491449     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00392-9     Document Type: Article

References (37)

1. For part 8, see: Juaristi, E.; López-Ruiz, H.; Madrigal, D.; Ramírez-Quirós, Y.; Escalante, J. J. Org. Chem. 1998, 63, 4706.
2. Presented in part during the Fifth Chemical Congress of North America, Cancún, México, November 13, 1997. Book of Abstracts, Paper No. 1476 ('Special Topics in Organic Chemistry').
3. See, for example: Jung, M. J. In Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; p. 227.
4. Paul, P. K. C.; Sukumar, M.; Bardi, R.; Piazzesi, A. M.; Valle, G.; Toniolo, C.; Balaram, P. J. Am. Chem. Soc. 1986, 108, 6363.
5. See, for example: Christensen, H. N.; Handlogten, M. E.; Vadgama, J. V.; de la Cuesta, E.; Ballesteros, P.; Trigo, G. C.; Avendaño, C. J. Med. Chem. 1983, 26, 1374.
6. See, for example: Turk, J.; Panse, G. T.; Marshall, G. R. J. Org. Chem. 1975, 40, 953.
7. See, for example: (a) Schoellkopf, U.; Hartwig, W.; Groth, U. Angew. Chem., Int. Ed. Engl. 1980, 19, 212. (b) Hunt, S. In Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; p. 55. (c) Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (d) Coppola, G. M.; Shuster, H. F. Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987; pp. 20, 78, 267. (e) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: London, 1989; pp. 1, 34, 62, 87, 208. (f) Ohfune, Y.; Moon, S. H.; Horikawa, M. Pure and Appl. Chem. 1996, 68, 645. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315. (h) Matsushita, M.; Maeda, H.; Kodama, M. Tetrahedron Lett. 1998, 39, 3749. (i) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225.
8. See, for example: (a) Schoellkopf, U.; Hartwig, W.; Groth, U. Angew. Chem., Int. Ed. Engl. 1980, 19, 212. (b) Hunt, S. In Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; p. 55. (c) Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (d) Coppola, G. M.; Shuster, H. F. Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987; pp. 20, 78, 267. (e) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: London, 1989; pp. 1, 34, 62, 87, 208. (f) Ohfune, Y.; Moon, S. H.; Horikawa, M. Pure and Appl. Chem. 1996, 68, 645. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315. (h) Matsushita, M.; Maeda, H.; Kodama, M. Tetrahedron Lett. 1998, 39, 3749. (i) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225.
9. See, for example: (a) Schoellkopf, U.; Hartwig, W.; Groth, U. Angew. Chem., Int. Ed. Engl. 1980, 19, 212. (b) Hunt, S. In Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; p. 55. (c) Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (d) Coppola, G. M.; Shuster, H. F. Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987; pp. 20, 78, 267. (e) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: London, 1989; pp. 1, 34, 62, 87, 208. (f) Ohfune, Y.; Moon, S. H.; Horikawa, M. Pure and Appl. Chem. 1996, 68, 645. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315. (h) Matsushita, M.; Maeda, H.; Kodama, M. Tetrahedron Lett. 1998, 39, 3749. (i) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225.
10. See, for example: (a) Schoellkopf, U.; Hartwig, W.; Groth, U. Angew. Chem., Int. Ed. Engl. 1980, 19, 212. (b) Hunt, S. In Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; p. 55. (c) Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (d) Coppola, G. M.; Shuster, H. F. Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987; pp. 20, 78, 267. (e) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: London, 1989; pp. 1, 34, 62, 87, 208. (f) Ohfune, Y.; Moon, S. H.; Horikawa, M. Pure and Appl. Chem. 1996, 68, 645. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315. (h) Matsushita, M.; Maeda, H.; Kodama, M. Tetrahedron Lett. 1998, 39, 3749. (i) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225.
11. See, for example: (a) Schoellkopf, U.; Hartwig, W.; Groth, U. Angew. Chem., Int. Ed. Engl. 1980, 19, 212. (b) Hunt, S. In Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; p. 55. (c) Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (d) Coppola, G. M.; Shuster, H. F. Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987; pp. 20, 78, 267. (e) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: London, 1989; pp. 1, 34, 62, 87, 208. (f) Ohfune, Y.; Moon, S. H.; Horikawa, M. Pure and Appl. Chem. 1996, 68, 645. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315. (h) Matsushita, M.; Maeda, H.; Kodama, M. Tetrahedron Lett. 1998, 39, 3749. (i) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225.
12. See, for example: (a) Schoellkopf, U.; Hartwig, W.; Groth, U. Angew. Chem., Int. Ed. Engl. 1980, 19, 212. (b) Hunt, S. In Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; p. 55. (c) Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (d) Coppola, G. M.; Shuster, H. F. Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987; pp. 20, 78, 267. (e) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: London, 1989; pp. 1, 34, 62, 87, 208. (f) Ohfune, Y.; Moon, S. H.; Horikawa, M. Pure and Appl. Chem. 1996, 68, 645. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315. (h) Matsushita, M.; Maeda, H.; Kodama, M. Tetrahedron Lett. 1998, 39, 3749. (i) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225.
13. See, for example: (a) Schoellkopf, U.; Hartwig, W.; Groth, U. Angew. Chem., Int. Ed. Engl. 1980, 19, 212. (b) Hunt, S. In Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; p. 55. (c) Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (d) Coppola, G. M.; Shuster, H. F. Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987; pp. 20, 78, 267. (e) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: London, 1989; pp. 1, 34, 62, 87, 208. (f) Ohfune, Y.; Moon, S. H.; Horikawa, M. Pure and Appl. Chem. 1996, 68, 645. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315. (h) Matsushita, M.; Maeda, H.; Kodama, M. Tetrahedron Lett. 1998, 39, 3749. (i) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225.
14. See, for example: (a) Schoellkopf, U.; Hartwig, W.; Groth, U. Angew. Chem., Int. Ed. Engl. 1980, 19, 212. (b) Hunt, S. In Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; p. 55. (c) Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (d) Coppola, G. M.; Shuster, H. F. Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987; pp. 20, 78, 267. (e) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: London, 1989; pp. 1, 34, 62, 87, 208. (f) Ohfune, Y.; Moon, S. H.; Horikawa, M. Pure and Appl. Chem. 1996, 68, 645. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315. (h) Matsushita, M.; Maeda, H.; Kodama, M. Tetrahedron Lett. 1998, 39, 3749. (i) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225.
15. See, for example: (a) Schoellkopf, U.; Hartwig, W.; Groth, U. Angew. Chem., Int. Ed. Engl. 1980, 19, 212. (b) Hunt, S. In Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; p. 55. (c) Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (d) Coppola, G. M.; Shuster, H. F. Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987; pp. 20, 78, 267. (e) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: London, 1989; pp. 1, 34, 62, 87, 208. (f) Ohfune, Y.; Moon, S. H.; Horikawa, M. Pure and Appl. Chem. 1996, 68, 645. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315. (h) Matsushita, M.; Maeda, H.; Kodama, M. Tetrahedron Lett. 1998, 39, 3749. (i) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225.
16. (a) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015, and references cited therein.
17. (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173, and references cited therein.
18. (a) Scott, W. L.; Zhou, C.; Fang, Z.; O'Donnell, M. J. Tetrahedron Lett. 1997, 38, 3695.
19. (b) Gaucher, A.; Bintein, F.; Wakselman, M.; Mazaleyrat, J. P. Tetrahedron Lett. 1998, 39, 575.
20. (c) Avenoza, A.; Cativiela, C.; París, M.; Peregrina, J. M. Tetrahedron: Asymmetry 1995, 6, 1409.
21. Juaristi, E.; Quintana, D. Tetrahedron: Asymmetry 1992, 3, 723.
22. Juaristi, E.; Quintana, D.; Balderas, M.; García-Pérez, E. Tetrahedron: Asymmetry 1996, 7, 2233.
23. 6). (figure presented)
24. DMPU has been recommended as solvent in various alkylation reactions. See Juaristi, E.; Murer, P.; Seebach, D. Synthesis 1993, 1243, and references cited therein.
25. Full details will be published elsewhere.
26. Juaristi, E.; Quintana, D.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1991, 56, 2553.
27. 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.
28. See, also: Juaristi, E.; Seebach, D. In Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; Chapter 13, pp. 261-277.
29. Schoellkopf, U.; Hausberg, H. H.; Hoppe, I.; Segal, M.; Reiter, U. Angew. Chem., Int. Ed. Engl. 1978, 17, 117.
30. Seebach, D.; Gees, T.; Schuler, F. Liebigs Ann. Chem. 1993, 785.
31. Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Weber, T. Helv. Chim. Acta 1987, 70, 237.
32. By contrast, no significant Lewis-acid assistance was observed upon addition of boron trifluoride etherate (0.3 equiv.) to the reaction medium.
33. Chambers, J. R.; Isbell, A. F. J. Org. Chem. 1964, 29, 832.
34. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. Organic Synthesis via Boranes; Wiley: New York, 1975; p. 256.
35. Juaristi, E.; Martínez-Richa, A.; García-Rivera, A.; Cruz-Sánchez, J. S. J. Org. Chem. 1983, 48, 2603.
36. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
37. When the heterocycle (100 mg) was dissolved in p-dioxane (3.0 ml), the hydrolysis reaction proceeded efficiently at 100°C, and was complete after 16 hours.