Abstract
As a result of the wide spectrum of applications of α- and β-amino acids, an unprecedented degree of activity has been recorded in the field of enantioselective synthesis of chiral amino acids. [1,2]
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References and Notes
M.J. O’Donnell, Ed., α-Amino Acid Synthesis (Tetrahedron Symposium-in-Print), Tetrahedron 44: 5253 (1988). (b) R.M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press: Oxford (1989). (c) R 0. Duthaler, Tetrahedron 50:1539 (1994).
E. Juaristi, D. Quintana, J. Escalante, Aldrichimica Acta 27: 3 (1994). (b) D.C. Cole, Tetrahedron 50:9517 (1994). (c) G. Cardillo, C. Tomasini, Chem. Soc. Rev. 25:117 (1996). (d) E. Juaristi, Ed., Enantioselective Synthesis of β-Amino Acids, Wiley-VCH: New York (1997).
U. Schoellkopf, Tetrahedron 39: 2085 (1983). (b) D. Seebach, E. Juaristi, D.D. Miller, C. Schickli, T. Weber, Helv. Chim. Acta 70:237 (1987). (c) R.M. Williams, P.J. Sinclair, D. Zhai, D. Chen, J. Am. Chem. Soc. 110:1547 (1988). (d) Y.N. Belokon, AS. Sagyan, S.M. Djamgaryan, V.I. Bakhmutov, V.M. Belikov, Tetrahedron 44:5507 (1988).
E. Juaristi, D. Seebach, in ref. 2d, Chapter 13, pp. 261–277. (b) G. Cardillo, C. Tomasini, in ref. 2d, Chapter 11, pp. 211-248. (c) J.P. Konopelski, in ref. 2d, Chapter 12, pp. 249-259.
R. Fitzi, D. Seebach, Tetrahedron 44: 5277 (1988). (b) D. Seebach, E. Dziadulewicz, L. Behrendt, S. Cantoreggi, R. Fitzi, Liebigs Ann. Chem. 1215 (1989).
E. Juaristi, D. Quintana, B. Lamatsch, D. Seebach, J. Org. Chem. 56: 2553 (1991).
K.S. Chu, G.R. Negrete, J.P. Konopelski, F.J. Lakner, N.T. Woo, M.M. Olmstead, J. Am. Chem. Soc, 114: 1800 (1992).
E. Juaristi, D. Quintana, Tetrahedron: Asymmetry 3: 723 (1992).
The assignment of the absolute configuration of dextrorotatory (S)-2 was accomplished by chemical correlation to levorotatory α-methyl-β-aminopropionic acid.
E. Juaristi, D. Quintana, M. Balderas, E. García-Pérez, Tetrahedron: Asymmetry 7: 2233 (1996).
M. J. Jung, In Chemistry and Biochemistry of the Amino Acids, G.C. Barrett, Ed., Chapman and Hall: New York (1985), p. 227. (b) P.K.C. Paul, M. Sukumar, R. Bardi, A.M. Piazzesi, G. Valle, C. Toniolo, P. Balaram, J. Am. Chem. Soc. 108:6363 (1986).
See, for example: (a) W.L. Scott, C. Zhou, Z. Fang, M.J. O’Donnell, Tetrahedron Lett. 38: 3695 (1997). (b) A. Gaucher, F. Bintein, M. Wakselman, J.P. Mazaleyrat, Tetrahedron Lett. 39:575 (1998).
M. Balderas, E. Juaristi, Unpublished results.
J.D. Aebi, D. Seebach, Helv. Chim. Acta 68: 1507 (1985). (b) A. Fadel, J. Salaün, Tetrahedron Lett. 28:2243 (1987). (c) G.I. Georg, X. Guan, J. Kant, Tetrahedron Lett. 29:403 (1988). (d) C.O. Chan, D. Crich, S. Natarajan, Tetrahedron Lett. 33:3405 (1992).
E. Juaristi, H. Lopez-Ruiz, D. Madrigal, Y. Ramírez-Quiros, J. Escalante, J. Org. Chem. 63: 0000(1998).
E. Juaristi, J. Escalante, J.L. León-Romo, A. Reyes, Tetrahedron: Asymmetry 9: 715(1998).
E. Juaristi, J.L. León-Romo, Y. Ramirez-Quirós, Unpublished results.
A. Reyes, E. Juaristi, Unpublished results.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1999 Springer Science+Business Media New York
About this chapter
Cite this chapter
Juaristi, E., Balderas, M., Luis León-Romo, J., López-Ruiz, H., Reyes, A. (1999). Stereoselective Alkylation of Chiral Glycine and Chiral β-Aminopropionic Acid Derivatives in the Preparation of Enantiopure α- and β-Amino Acids. In: Scolastico, C., Nicotra, F. (eds) Current Trends in Organic Synthesis. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4801-0_25
Download citation
DOI: https://doi.org/10.1007/978-1-4615-4801-0_25
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4613-7175-5
Online ISBN: 978-1-4615-4801-0
eBook Packages: Springer Book Archive