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Volumn 14, Issue 15, 2003, Pages 2229-2238

Efficient synthesis of β-halogeno protected L-alanines and their β-phosphonium derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE DERIVATIVE; AMINO ACID; BROMINE DERIVATIVE; ESTER DERIVATIVE; HALIDE; OXAZOLINE DERIVATIVE; PHOSPHONIUM DERIVATIVE; SERINE DERIVATIVE; TRIPHENYLPHOSPHINE;

EID: 0042198699     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00484-1     Document Type: Article
Times cited : (14)

References (45)
  • 11
    • 0002563284 scopus 로고    scopus 로고
    • For a review of the free-radical reactions in the synthesis of amino acids, see:
    • For a review of the free-radical reactions in the synthesis of amino acids, see: Easton C.J. Chem. Rev. 97:1997;53-82.
    • (1997) Chem. Rev. , vol.97 , pp. 53-82
    • Easton, C.J.1
  • 20
    • 0022354620 scopus 로고    scopus 로고
    • For a pertinent synthesis of β-halogeno amino acids derivatives from serine, see: (a) Arnold, L. D.; Kalantar, T. H.; Vederas, J. C. J. Am. Chem. Soc. 1985, 107, 7105-7109; (b) Ref. 4a; (c) Ref. 3b.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 7105-7109
    • Arnold, L.D.1    Kalantar, T.H.2    Vederas, J.C.3
  • 21
    • 0022354620 scopus 로고    scopus 로고
    • (b) Ref. 4a
    • For a pertinent synthesis of β-halogeno amino acids derivatives from serine, see: (a) Arnold, L. D.; Kalantar, T. H.; Vederas, J. C. J. Am. Chem. Soc. 1985, 107, 7105-7109; (b) Ref. 4a; (c) Ref. 3b.
  • 22
    • 0022354620 scopus 로고    scopus 로고
    • (c) Ref. 3b
    • For a pertinent synthesis of β-halogeno amino acids derivatives from serine, see: (a) Arnold, L. D.; Kalantar, T. H.; Vederas, J. C. J. Am. Chem. Soc. 1985, 107, 7105-7109; (b) Ref. 4a; (c) Ref. 3b.
  • 27
    • 0018898035 scopus 로고    scopus 로고
    • Ref. 9a
    • For a representative synthesis of β-bromo or iodo L-alanine with a free acidic function, see: (a) Ref. 9a; (b) Shiue, C.-Y.; Wolf, A. P. J. Labelled Compd. Radiopharm. 1980, 17, 53-58.
  • 28
    • 0018898035 scopus 로고    scopus 로고
    • For a representative synthesis of β-bromo or iodo L-alanine with a free acidic function, see: (a) Ref. 9a; (b) Shiue, C.-Y.; Wolf, A. P. J. Labelled Compd. Radiopharm. 1980, 17, 53-58.
    • (1980) J. Labelled Compd. Radiopharm. , vol.17 , pp. 53-58
    • Shiue, C.-Y.1    Wolf, A.P.2
  • 29
    • 85031140994 scopus 로고    scopus 로고
    • Under the liquid chromatography conditions, the formation of the oxazoline 2 from 3 was observed
    • Under the liquid chromatography conditions, the formation of the oxazoline 2 from 3 was observed.
  • 37
    • 85031144196 scopus 로고    scopus 로고
    • Crystallographic data for 2a has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 209373. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: 44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk]
    • Crystallographic data for 2a has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 209373. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: 44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
  • 38
    • 0000925315 scopus 로고
    • For the preparation of (±)-oxazoline 2b see: (a) Black, D. St. C.; Wade, M. J. Aust. J. Chem. 1972, 25, 1797-1810; (b) Reider, P. J.; Eichen Conn, R. S.; Davis, P.; Grenda, V. J.; Zambito, A. J.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 3326-3334.
    • (1972) Aust. J. Chem. , vol.25 , pp. 1797-1810
  • 43
    • 85031135838 scopus 로고    scopus 로고
    • The chloroform used was stabilized with amylene rather than EtOH in order to avoid transesterification or the formation of by-products
    • The chloroform used was stabilized with amylene rather than EtOH in order to avoid transesterification or the formation of by-products.
  • 44
    • 85031141130 scopus 로고    scopus 로고
    • The procedure requires water, which corrects the previous and incomplete description reported in Ref. 7
    • The procedure requires water, which corrects the previous and incomplete description reported in Ref. 7.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.