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Volumn 61, Issue 8, 1996, Pages 2582-2583

An enantiomeric synthesis of allo-threonines and β-hydroxyvalines

Author keywords

[No Author keywords available]

Indexed keywords

BETA HYDROXYVALINE; THREONINE; UNCLASSIFIED DRUG;

EID: 0029895657     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960141c     Document Type: Article
Times cited : (56)

References (44)
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    • Leading references of β-hydroxy α-amino acids: (a) Duthaler, B. G.; Riediker, M. Angew. Chem., Int. Ed. Engl 1989, 28, 497-498. (b) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron. Lett. 1987,28, 39-42. (c) Roemmele, R. C.; Rapoport, J. J. Org. Chem. 1989, 54, 1866-1875 and references cited therein. (d) Wipf, P. Miller, C. P. J. Org. Chem. 1993, 58, 1575-1578 and references cited therein. (e) Okonya, J. F.; Kolasa, T.; Miller, M. J. Ibid. 1905, 60, 1932-1935. (f) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827-830. (g) Schollkopf, U. Tetrahedron 1983, 39, 2085. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C. Weber, T. Helv. Chim. Acta 1987, 70, 237-261. (i) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757-6761.
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    • (1983) Tetrahedron , vol.39 , pp. 2085
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    • For the synthesis of derivatives of β-hydroxyvalme, see: (a) Ciufolim, M. A.; Swaminathan, S. Tetrahedron Lett. 1989, 30, 3027-3028. (b) Schöllkopf, U.; Nozulak, J.; Groth, U. Synthesis 1982, 868-870. (c) Hanson, R. L.; Singh, J.; Kissick, T. P.; Patel, R. N.; Szarka, L. J.; Mueller, R. H. Bioorg. Chem. 1990, 18, 116-130.
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    • For reviews of the AD reactions, see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 2483-2547. (b) Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059-1070. (c) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp 227-272.
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    • For reviews of the AD reactions, see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 2483-2547. (b) Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059-1070. (c) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp 227-272.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 1059-1070
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    • Ojima, I., Ed.; VCH Publishers: New York
    • For reviews of the AD reactions, see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 2483-2547. (b) Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059-1070. (c) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp 227-272.
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    • note
    • The enantiomeric excesses of all compounds were determined by the HPLC method using a Chiralcel OD column with hexane and 2-propanol as the eluents.


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