α-Alkylation of (S)-Asparagine with Self-Regeneration of the Stereogenic Center: Enantioselective Synthesis of α-Substituted Aspartic Acids

Journal of Organic Chemistry

Volumn 63, Issue 14, 1998, Pages 4706-4710

  Juaristi, Eusebio ^a   López Ruiz, Heraclio ^a   Madrigal, Domingo ^a   Ramírez Quirós, Yara ^a   Escalante, Jaime ^a  

^a DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000680481     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980367a     Document Type: Article

References (33)

1. Enantioselective synthesis of β-amino acids. 8. For part 7 see: Juaristi, E.; Quintana, D.; Balderas, M.; García-Pérez, E. Tetrahedron: Asymmetry 1996, 7, 2233-2246.
2. Presented in part during the Fifth Chemical Congress of North America, Cancún, México, November 13, 1997. Special Topics in Organic Chemistry. In Book of Abstracts, Paper No. 1476.
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.
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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, 1374-1378.
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8. See, also: Altmann, E.; Nebel, K.; Mutter, M. Helv. Chim. Acta 1991, 74, 800-806.
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12. More recently, Obrecht and co-workers described the availability of (R)- and (S)-α-alkyl aspartic acids using L-phenylalanine as resolving agent: Obrecht, D.; Bohdal, U.; Daly, J.; Lehmann, C.; Schönholzer, P.; Müller, K. Tetrahedron 1995, 51, 10883-10900.
13. (a) Chu, K. S.; Negrete, G. R.; Konopelski, J. P. J. Org. Chem. 1991, 56, 5196-5202.
14. (b) See, also: Konopelski, J. P. In Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; Chapter 12, pp 249-259.
15. (a) Juaristi, E.; Quintana, D. Tetrahedron: Asymmetry 1992, 3, 723-726.
16. (b) 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.
17. Owing to the high price of pivalaldehyde, we have substituted this aldehyde with isobutyraldehyde in the synthesis of some chiral analogues of pyrimidinone 6: Madrigal, D. Ph.D. Thesis, CINVESTAV-IPN: México, 1996.
18. The authors have deposited atomic coordinates for structures cis-8 and (2S,6S)-13 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, CB2 IEZ, U.K.
19. (a) Compare mild conditions employed to hydrolyze bislactimethers: Schöllkopf, U.; Tiller, T.; Bardenhagen, J. Tetrahedron 1988, 44, 5293-5305.
20. (b) Compare mild conditions used to hydrolyze dihydroimidazoles: Hoffmann, M.; Seebach, D. Chimia 1997, 51, 90-91. Blank, S.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1993, 32, 1765-1766.
21. (b) Compare mild conditions used to hydrolyze dihydroimidazoles: Hoffmann, M.; Seebach, D. Chimia 1997, 51, 90-91. Blank, S.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1993, 32, 1765-1766.
22. (c) For related papers, see: Seebach, D.; Hoffmann, M.; Sting, A. R.; Kinkel, J. N.; Schulte, M.; Küsters, E. J. Chromatogr. A 1998, 796, 299-307. Hoffmann, M.; Blank, S.; Seebach, D.; Küsters, E.; Schmid, E. Chirality 1998, 10, 217-222.
23. (c) For related papers, see: Seebach, D.; Hoffmann, M.; Sting, A. R.; Kinkel, J. N.; Schulte, M.; Küsters, E. J. Chromatogr. A 1998, 796, 299-307. Hoffmann, M.; Blank, S.; Seebach, D.; Küsters, E.; Schmid, E. Chirality 1998, 10, 217-222.
24. 13C NMR spectroscopy (400 and 100 MHz, respectively).
25. Compare (a) Juaristi, E.; Escalante, J.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1992, 57, 2396-2398. (b) Juaristi, E.; Escalante, J. J. Org. Chem. 1993, 58, 2282-2285. (c) Escalante, J.; Juaristi, E. Tetrahedron Lett. 1995, 36, 4397-4400.
26. Compare (a) Juaristi, E.; Escalante, J.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1992, 57, 2396-2398. (b) Juaristi, E.; Escalante, J. J. Org. Chem. 1993, 58, 2282-2285. (c) Escalante, J.; Juaristi, E. Tetrahedron Lett. 1995, 36, 4397-4400.
27. Compare (a) Juaristi, E.; Escalante, J.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1992, 57, 2396-2398. (b) Juaristi, E.; Escalante, J. J. Org. Chem. 1993, 58, 2282-2285. (c) Escalante, J.; Juaristi, E. Tetrahedron Lett. 1995, 36, 4397-4400.
28. Compare (a) Juaristi, E.; Quintana, D.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1991, 56, 2553-2557. (b) 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, 913-934.
29. Compare (a) Juaristi, E.; Quintana, D.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1991, 56, 2553-2557. (b) 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, 913-934.
30. Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748.
31. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. Organic Synthesis via Boranes; Wiley: New York, 1975; p 256.
32. Juaristi, E.; Martínez-Richa, A.; García-Rivera, A.; Cruz-Sánchez, J. S. J. Org. Chem. 1983, 48, 2603-2606.
33. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.