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Volumn 39, Issue 33, 1998, Pages 5887-5890

1,3-Asymmetric induction in dianionic allylation reactions of amino acid derivatives-synthesis of functionally useful enantiopure glutamates, pipecolates and pyroglutamates

Author keywords

Allylation; Amino acids and derivatives; Asymmetric induction; Peptide analogs mimetics

Indexed keywords

AMINO ACID DERIVATIVE; GLUTAMIC ACID; PIPECOLIC ACID; PYROGLUTAMIC ACID;

EID: 0032514576     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00900-9     Document Type: Article
Times cited : (75)

References (53)
  • 13
    • 0002651548 scopus 로고
    • Bergmann, E.; Pullman, B. Eds.; D. Reidel Publishing
    • b) Ham, N. S. in "Molecular and Quantum Pharmacology", Bergmann, E.; Pullman, B. Eds.; D. Reidel Publishing, 1974, p. 261.
    • (1974) Molecular and Quantum Pharmacology , pp. 261
    • Ham, N.S.1
  • 27
    • 0031032162 scopus 로고    scopus 로고
    • Possible transition state models: (formula presented)
    • [9] Hanessian, S; Schaum, R. Tetrahedron Lett., 1997, 38, 163; Possible transition state models: (formula presented)
    • (1997) Tetrahedron Lett. , vol.38 , pp. 163
    • Hanessian, S.1    Schaum, R.2
  • 32
    • 0010491792 scopus 로고    scopus 로고
    • See for example: a) ref 6b
    • [13] See for example: a) ref 6b;
  • 40
    • 0010451623 scopus 로고    scopus 로고
    • note
    • [15] Typical procedure: a solution of substrate (1 mmol) was dissolved in dry THF (4 ml) and added dropwise (via cannula) to a stirring solution of LiHMDS (2.1 mmol, Aldrich 1M in THF). After about 30 min. freshly distilled allyl iodide or bromide (3 mmol, neat) was added and the reaction mixture was stirred at -78°C until disappearance of the starting material. Quenching with 10% HCl (-78°C), work-up and silica gel flash chromatography (hexanes/AcOEt) provided the desired alkylated compound.


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