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Volumn 55, Issue 41, 1999, Pages 12031-12044

Stereochemically defined C-substituted glutamic acids and their derivatives. 1. An efficient asymmetric synthesis of (2S,3S)-3-methyl- and - 3-trifluoromethylpyroglutamic acids

Author keywords

Addition reactions; Amino acids and derivatives; Asymmetric synthesis; Mechanism; Nickel

Indexed keywords

AMINO ACID DERIVATIVE; BENZYL DERIVATIVE; GLUTAMIC ACID DERIVATIVE; GLYCINE; METHYL GROUP; NICKEL; PYROGLUTAMIC ACID; SCHIFF BASE;

EID: 0033536721     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00711-5     Document Type: Article
Times cited : (98)

References (54)
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    • Refs. 1-69 in the review 1a
    • (f) Refs. 1-69 in the review 1a.
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    • note
    • Separation of the target amino acids from valine is usually achieved by bulb-to-bulb distillation, or by anion exchange chromatography under controlled pH conditions.
  • 26
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    • note
    • The reactions of tert-butyl (S)-2-tert-butyl-3-methyl-4-oxo-1-imidazolidinecarboxylate (Boc-BMI) with methyl or ethyl crotonates afford a mixture of the corresponding 3-methylglutamic acid derivatives in 58% and 68% yield respectively; Diastereoselectivity of the reaction ranges from 20-40% de favoring (2S,3R)-configured diastereomers; for details see ref. 9.
  • 28
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    • note
    • The stereochemistry of the products obtained in the reaction between rac-tert-butyl 2-tert-butyl-methoxy- 2,5-dihydroimidazole-1-carboxylate and 2,6-di-tert-butyl-4-methoxyphenylbut-2-enecarboxylate has not been assigned; for details see ref. 2b.
  • 29
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    • note
    • Provided, of course, efficient procedures for preparing these derivatives and further release of a free carboxylic group.
  • 31
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    • The relative amount of the fourth diastereomer has not been provided; see ref. 12
    • The relative amount of the fourth diastereomer has not been provided; see ref. 12.
  • 38
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    • Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, D. C.; Chapter 2
    • (d) Soloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, D. C., 1996; Chapter 2.
    • (1996) Biomedical Frontiers of Fluorine Chemistry
    • Soloshonok, V.A.1
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    • note
    • 3/acetone or acetone/n-hexane).
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    • note
    • 1H-NMR spectra of the complexes containing α-(L)- and α-(D)-amino acids also are very characteristic featuring substantial difference in chemical shifts of aromatic and methylene protons of the (N-benzyl)proline moiety.
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    • Eliel, E. L.; Wilen, S. H., Eds.; Wiley: New York
    • (a) Oare, D. A.; Heathcock, C. H. Topics in Stereochemistry, Eliel, E. L.; Wilen, S. H., Eds.; Wiley: New York, 1990, vol. 19, p. 227-407.
    • (1990) Topics in Stereochemistry , vol.19 , pp. 227-407
    • Oare, D.A.1    Heathcock, C.H.2
  • 53
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    • For discussions on the stereochemical properties of fluorine-containing substituents and trifluoromethyl group, in particular, see ref. 23
    • For discussions on the stereochemical properties of fluorine-containing substituents and trifluoromethyl group, in particular, see ref. 23.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.