Practical synthesis of Schollkopf's bis-lactim ether chiral auxiliary: (3S)-3,6-dihydro-2,5-dimethoxy-3-isopropyl-pyrazine

Tetrahedron Asymmetry

Volumn 9, Issue 2, 1998, Pages 321-327

  Bull, Steven D ^a   Davies, Stephen G ^a   Moss, William O ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3,6 DIHYDRO 2,5 DIMETHOXY 3 ISOPROPYLPYRAZINE; GELLING AGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; TEMPERATURE;

EID: 0032579180     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00623-X     Document Type: Article

References (25)

1. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press, 1989; H. Heimgartner, Angew. Chem. Int. Ed. Engl., 1991, 30, 238; R. O. Duthaler, Tetrahedron, 1994, 50, 1539; D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. Int. Ed. Engl., 1996, 35, 2708; T. Wirth, Angew. Chem. Int. Ed. Engl., 1997, 36, 225; R. Chinchilla, L. R. Falvello, N. Galindo, C. Nájera, Angew. Chem. Int. Ed. Engl., 1997, 36, 995.
2. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press, 1989; H. Heimgartner, Angew. Chem. Int. Ed. Engl., 1991, 30, 238; R. O. Duthaler, Tetrahedron, 1994, 50, 1539; D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. Int. Ed. Engl., 1996, 35, 2708; T. Wirth, Angew. Chem. Int. Ed. Engl., 1997, 36, 225; R. Chinchilla, L. R. Falvello, N. Galindo, C. Nájera, Angew. Chem. Int. Ed. Engl., 1997, 36, 995.
3. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press, 1989; H. Heimgartner, Angew. Chem. Int. Ed. Engl., 1991, 30, 238; R. O. Duthaler, Tetrahedron, 1994, 50, 1539; D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. Int. Ed. Engl., 1996, 35, 2708; T. Wirth, Angew. Chem. Int. Ed. Engl., 1997, 36, 225; R. Chinchilla, L. R. Falvello, N. Galindo, C. Nájera, Angew. Chem. Int. Ed. Engl., 1997, 36, 995.
4. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press, 1989; H. Heimgartner, Angew. Chem. Int. Ed. Engl., 1991, 30, 238; R. O. Duthaler, Tetrahedron, 1994, 50, 1539; D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. Int. Ed. Engl., 1996, 35, 2708; T. Wirth, Angew. Chem. Int. Ed. Engl., 1997, 36, 225; R. Chinchilla, L. R. Falvello, N. Galindo, C. Nájera, Angew. Chem. Int. Ed. Engl., 1997, 36, 995.
5. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press, 1989; H. Heimgartner, Angew. Chem. Int. Ed. Engl., 1991, 30, 238; R. O. Duthaler, Tetrahedron, 1994, 50, 1539; D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. Int. Ed. Engl., 1996, 35, 2708; T. Wirth, Angew. Chem. Int. Ed. Engl., 1997, 36, 225; R. Chinchilla, L. R. Falvello, N. Galindo, C. Nájera, Angew. Chem. Int. Ed. Engl., 1997, 36, 995.
6. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press, 1989; H. Heimgartner, Angew. Chem. Int. Ed. Engl., 1991, 30, 238; R. O. Duthaler, Tetrahedron, 1994, 50, 1539; D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. Int. Ed. Engl., 1996, 35, 2708; T. Wirth, Angew. Chem. Int. Ed. Engl., 1997, 36, 225; R. Chinchilla, L. R. Falvello, N. Galindo, C. Nájera, Angew. Chem. Int. Ed. Engl., 1997, 36, 995.
7. C. Deng, U. Groth, U. Schöllkopf, Angew. Chem. Int. Ed. Engl., 1981, 21, 798; U. Schöllkopf, Pure Appl. Chem., 1983, 55, 1799; U. Schöllkopf, U. Busse, R. Lonsky, R. Hinrichs, Liebigs Ann. Chem., 1986, 2150.
8. C. Deng, U. Groth, U. Schöllkopf, Angew. Chem. Int. Ed. Engl., 1981, 21, 798; U. Schöllkopf, Pure Appl. Chem., 1983, 55, 1799; U. Schöllkopf, U. Busse, R. Lonsky, R. Hinrichs, Liebigs Ann. Chem., 1986, 2150.
9. C. Deng, U. Groth, U. Schöllkopf, Angew. Chem. Int. Ed. Engl., 1981, 21, 798; U. Schöllkopf, Pure Appl. Chem., 1983, 55, 1799; U. Schöllkopf, U. Busse, R. Lonsky, R. Hinrichs, Liebigs Ann. Chem., 1986, 2150.
10. Recent examples where 1 has been successfully employed for the asymmetric synthesis of complex non proteinogenic α-amino acids include V. Ojea, C. Fernández, M. Ruiz, J. M. Quintela, Tetrahedron Lett., 1996, 32, 5801; A. J. Pearson, H. Shin, J. Org. Chem., 1994, 59, 2314; R. Mueller, L. Revesz, Tetrahedron Lett., 1994, 35, 4091; M. Ohba, T. Mukaihira, T. Fujii, Chem. Pharm. Bull., 1994, 42, 1784; J. Paladino, C. Guyard, C. Thurieau, J. Fauchère, Helv. Chim. Acta., 1993, 76, 2465; J. E. Baldwin, R. M. Adlington, M. B. Mitchell, J. Chem. Soc., Chem. Commun., 1993, 1332.
11. Recent examples where 1 has been successfully employed for the asymmetric synthesis of complex non proteinogenic α-amino acids include V. Ojea, C. Fernández, M. Ruiz, J. M. Quintela, Tetrahedron Lett., 1996, 32, 5801; A. J. Pearson, H. Shin, J. Org. Chem., 1994, 59, 2314; R. Mueller, L. Revesz, Tetrahedron Lett., 1994, 35, 4091; M. Ohba, T. Mukaihira, T. Fujii, Chem. Pharm. Bull., 1994, 42, 1784; J. Paladino, C. Guyard, C. Thurieau, J. Fauchère, Helv. Chim. Acta., 1993, 76, 2465; J. E. Baldwin, R. M. Adlington, M. B. Mitchell, J. Chem. Soc., Chem. Commun., 1993, 1332.
12. Recent examples where 1 has been successfully employed for the asymmetric synthesis of complex non proteinogenic α-amino acids include V. Ojea, C. Fernández, M. Ruiz, J. M. Quintela, Tetrahedron Lett., 1996, 32, 5801; A. J. Pearson, H. Shin, J. Org. Chem., 1994, 59, 2314; R. Mueller, L. Revesz, Tetrahedron Lett., 1994, 35, 4091; M. Ohba, T. Mukaihira, T. Fujii, Chem. Pharm. Bull., 1994, 42, 1784; J. Paladino, C. Guyard, C. Thurieau, J. Fauchère, Helv. Chim. Acta., 1993, 76, 2465; J. E. Baldwin, R. M. Adlington, M. B. Mitchell, J. Chem. Soc., Chem. Commun., 1993, 1332.
13. Recent examples where 1 has been successfully employed for the asymmetric synthesis of complex non proteinogenic α-amino acids include V. Ojea, C. Fernández, M. Ruiz, J. M. Quintela, Tetrahedron Lett., 1996, 32, 5801; A. J. Pearson, H. Shin, J. Org. Chem., 1994, 59, 2314; R. Mueller, L. Revesz, Tetrahedron Lett., 1994, 35, 4091; M. Ohba, T. Mukaihira, T. Fujii, Chem. Pharm. Bull., 1994, 42, 1784; J. Paladino, C. Guyard, C. Thurieau, J. Fauchère, Helv. Chim. Acta., 1993, 76, 2465; J. E. Baldwin, R. M. Adlington, M. B. Mitchell, J. Chem. Soc., Chem. Commun., 1993, 1332.
14. Recent examples where 1 has been successfully employed for the asymmetric synthesis of complex non proteinogenic α-amino acids include V. Ojea, C. Fernández, M. Ruiz, J. M. Quintela, Tetrahedron Lett., 1996, 32, 5801; A. J. Pearson, H. Shin, J. Org. Chem., 1994, 59, 2314; R. Mueller, L. Revesz, Tetrahedron Lett., 1994, 35, 4091; M. Ohba, T. Mukaihira, T. Fujii, Chem. Pharm. Bull., 1994, 42, 1784; J. Paladino, C. Guyard, C. Thurieau, J. Fauchère, Helv. Chim. Acta., 1993, 76, 2465; J. E. Baldwin, R. M. Adlington, M. B. Mitchell, J. Chem. Soc., Chem. Commun., 1993, 1332.
15. Recent examples where 1 has been successfully employed for the asymmetric synthesis of complex non proteinogenic α-amino acids include V. Ojea, C. Fernández, M. Ruiz, J. M. Quintela, Tetrahedron Lett., 1996, 32, 5801; A. J. Pearson, H. Shin, J. Org. Chem., 1994, 59, 2314; R. Mueller, L. Revesz, Tetrahedron Lett., 1994, 35, 4091; M. Ohba, T. Mukaihira, T. Fujii, Chem. Pharm. Bull., 1994, 42, 1784; J. Paladino, C. Guyard, C. Thurieau, J. Fauchère, Helv. Chim. Acta., 1993, 76, 2465; J. E. Baldwin, R. M. Adlington, M. B. Mitchell, J. Chem. Soc., Chem. Commun., 1993, 1332.
16. 1 is commercially available in limited quantities at high cost (£219 for 5 ml) from Fluka/Merck-Schuchardt.
17. J. E. Rose, P. D. Leeson, D. Gani, J. Chem. Soc., Perkin Trans. 1, 1995, 157.
18. These figures compare favourably with other gelling agents of low molecular weight; K. Hanabusa, Y. Matsumoto, T. Miki, T. Koyama, H. Shirai, J. Chem. Soc., Chem. Commun., 1994, 1401; H. T. Stock, N. J. Turner, R. McCague, J. Chem. Soc., Chem. Commun., 1995, 2063.
19. These figures compare favourably with other gelling agents of low molecular weight; K. Hanabusa, Y. Matsumoto, T. Miki, T. Koyama, H. Shirai, J. Chem. Soc., Chem. Commun., 1994, 1401; H. T. Stock, N. J. Turner, R. McCague, J. Chem. Soc., Chem. Commun., 1995, 2063.
20. 1H NMR spectra which enable subsequent alkylation diastereoselectivities to be easily determined.
21. T. J. Curphey, Organic Synthesis. Coll. Vol. VI, 1988, John Wiley, New York.
22. 2O afforded inferior yields of 1 although this method is an excellent way of preparing bis-benzylated auxiliary 11; U. Groth, C. Schmeck, U. Schöllkopf, Liebigs. Ann. Chem., 1993, 321.
23. R. Appel, G. Bäumer, W. Strüver, Chem. Ber., 1975, 108, 2680.
24. Penicillamine-based 12 is particularly noteworthy because of the ease of separation of the parent α-amino acids methyl esters by extraction of the penicillamine ester trifluoroacetate salt, into dichloromethane enabling the desired α-amino acid to be recovered from the aqueous layer; L. S. Richter, T. R. Gadek, Tetrahedron: Asymmetry, 1996, 6, 427.
25. T. Weihrauch, D. Leibfritz, Liebigs. Ann. Chem., 1985, 1917.