The Stereoselective Synthesis of a-Amino Acids by Phase-Transfer Catalysis

Journal of the American Chemical Society

Volumn 111, Issue 6, 1989, Pages 2353-2355

  O'Donnell, Martin J ^a   Bennett, William D ^a   Wu, Shengde ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845185214     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00188a089     Document Type: Article

References (17)

1. a-Amino Acid Synthesis; O'Donnell, M. J., Ed. Tetrahedron Symposium-in-Print, Pergamon: London, 1988; Vol. 44, Issue 17. (b) Barrett, G. C. Chemistry and Biochemistry of the Amino Acids; Chapman and Hall: London, 1985. (c) Amino Acids, Peptides and Proteins; Specialist Periodical Reports, The Royal Society of Chemistry: London, 1969-1985; Vol. 1–16. (d) Amino Acids and Peptides; Specialist Periodical Reports, The Royal Society of Chemistry: London, 1986-1987; Vol. 17–18.
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4. a-H bond formation (“deracemization”): Duhamel, L.; Duhamel, P.; Fouquay, S.; Eddine, J. J.; Peschard, O.; Plaquevant, J.-C.; Ravard, A.; Solliard, R.; Valnot, J.-Y.; Vincens, H. Tetrahedron 1988, 44, 5495–5506, and cited references.
5. a-N bond formation: (a) Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F., Jr. Tetrahedron 1988, 44, 5525–5540. (b) Oppolzer, W., Moretti, R. Tetrahedron 1988, 44, 5541–5552. (c) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553–5562. (d) Cardani, S.; Bernardi, A.; Colombo, L.; Gennari, C.; Scolastico, C.; Venturini, I. Tetrahedron 1988, 44, 5563–5572, and cited references.
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8. Other syntheses of amino acid derivatives involving phase-transfer reactions: (a) Schöllkopf, U.; Hoppe, D.; Jentsch, R. Chem. Ber. 1975, 108, 1580–1592. (b) Beck, W.; Girnth, M. Chem. Ber. 1976, 109, 965–969. (c) Schöllkopf, U.; Hausberg, H. H.; Hoppe, I.; Segal, M.; Reiter, U. Angew. Chem., Int. Ed. Engl. 1978, 17, 117–119. (d) Juliá, S.; Ginebreda, A.; Guixer, J. Chem. Commun. 1978, 742–743. (e) Landini, D.; Montanari, F.; Rolla, F. Synthesis 1979, 26–27. (f) Kolodziejczyk, A. M.; Arendt, A. Polish J. Chem. 1980, 54, 1327–1329. (g) Gelmi, M. L.; Pocar, D.; Rossi, L. M. Synthesis 1984, 763–765. (h) Belokon', Y. N.; Chernoglazova, N. I.; Kochetkov, C. A.; Garbalinskaya, N. S.; Belikov, V. M. Chem. Commun. 1985, 171–172. (i) Bram, G.; Galons, H.; Farnoux, C. C.; Miocque, M. Pharmazie 1987, 42, 199; Chem. Abstr. 1988, 108:112906e. (j) Yu, L.; Wang, F. Gaodeng Xuexiao Huaxue Xuebao 1987, 8, 336-340; Chem. Abstr. 1988, 108:112909h. (k) Jiang, Y.; Zhou, C.; Wu, S.; Chen, D.; Ma, Y.; Liu, G. Tetrahedron 1988, 44, 5343–5353, and cited references.
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11. 7dfrom benzophenone imine (Aldrich or Pickard, P. L.; Tolbert, T. L. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. 5, pp 520–522) and glycine tert-butyl ester hydrochloride (Sigma or Moore, A. T.; Rydon, H. N. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. 5, pp 586–589).
12. Wynberg, H. Recl. Trav. Chim. 1981, 100, 393–399.
13. Wynberg, H.; Chemtech 1982, 116-121.
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15. Yamada, H.; Shimizu, S. Angew. Chem., Int. Ed. Engl. 1988, 27, 622–642.
16. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; Wiley-Interscience: New York, 1981.
17. “.racemic compound crystals are generally more stable than enantiomer crystals.” Reference 17, p 28. (b) For a recent example, see: Bhattacharya, A.; Dolling, U.-H.; Grabowski, E. J. J.; Karady, S.; Ryan, K. M.; Weinstock, L. M. Angew. Chem., Int. Ed. Enzl. 1986. 25, 476–477.