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Volumn 38, Issue 26, 1997, Pages 4671-4674

Highly diastereoselective aza-aldol reactions of a chiral Ni(II) complex of glycine with imines. An efficient asymmetric approach to 3-perfluoroalkyl-2,3-diamino acids

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE;

EID: 0030961675     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00963-5     Document Type: Article
Times cited : (100)

References (28)
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    • Pergamon Press, Oxford
    • For comprehensive reviews on the asymmetric synthesis of α-and β-amino acids see: (α-amino acids) (a) Williams, R. Synthesis of Optically Active α-Amino Acids, Pergamon Press, Oxford, 1989; and
    • (1989) Synthesis of Optically Active α-Amino Acids
    • Williams, R.1
  • 2
    • 0028355337 scopus 로고
    • β-amino acids
    • (b) Duthaler, R. P. Tetrahedron 1994, 50, 1539; (β-amino acids)
    • (1994) Tetrahedron , vol.50 , pp. 1539
    • Duthaler, R.P.1
  • 10
    • 0344746480 scopus 로고    scopus 로고
    • Biocatalytic entry to enantiomerically pure β-Amino acids
    • Juaristi, E. Ed., VCH Publishers, INC., N.Y., Chapter 21
    • (b) Soloshonok, V. A. "Biocatalytic Entry to Enantiomerically Pure β-Amino Acids" in Enantioselective Synthesis of β-Amino Acids, Juaristi, E. Ed., VCH Publishers, INC., N.Y., Chapter 21, 1996;
    • (1996) Enantioselective Synthesis of β-Amino Acids
    • Soloshonok, V.A.1
  • 11
    • 0011879122 scopus 로고    scopus 로고
    • Practical synthesis of enantiopure fluoro-amino acids of biological interest by asymmetric aldol reactions
    • Ojima, I.; McCarthy, J. R.; Welch, J. T. Eds., ACS Books, American Chemical Society, Washington, D.C., Chapter 2
    • (c) Soloshonok, V. A. "Practical Synthesis of Enantiopure Fluoro-Amino Acids of Biological Interest by Asymmetric Aldol Reactions" in Biomedical Frontiers of Fluorine Chemistry, Ojima, I.; McCarthy, J. R.; Welch, J. T. Eds., ACS Books, American Chemical Society, Washington, D.C., Chapter 2, 1996; For most recent publications see: Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print, 58; Tetrahedron 1996, 52, 1-330.
    • (1996) Biomedical Frontiers of Fluorine Chemistry
    • Soloshonok, V.A.1
  • 12
    • 0010790603 scopus 로고    scopus 로고
    • (c) Soloshonok, V. A. "Practical Synthesis of Enantiopure Fluoro-Amino Acids of Biological Interest by Asymmetric Aldol Reactions" in Biomedical Frontiers of Fluorine Chemistry, Ojima, I.; McCarthy, J. R.; Welch, J. T. Eds., ACS Books, American Chemical Society, Washington, D.C., Chapter 2, 1996; For most recent publications see: Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print, 58; Tetrahedron 1996, 52, 1-330.
    • Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards
    • Resnati, G.1    Soloshonok, V.A.2
  • 13
    • 0343700223 scopus 로고    scopus 로고
    • (c) Soloshonok, V. A. "Practical Synthesis of Enantiopure Fluoro-Amino Acids of Biological Interest by Asymmetric Aldol Reactions" in Biomedical Frontiers of Fluorine Chemistry, Ojima, I.; McCarthy, J. R.; Welch, J. T. Eds., ACS Books, American Chemical Society, Washington, D.C., Chapter 2, 1996; For most recent publications see: Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print, 58; Tetrahedron 1996, 52, 1-330.
    • Tetrahedron Symposium-in-Print , vol.58
  • 14
    • 0001834676 scopus 로고    scopus 로고
    • (c) Soloshonok, V. A. "Practical Synthesis of Enantiopure Fluoro-Amino Acids of Biological Interest by Asymmetric Aldol Reactions" in Biomedical Frontiers of Fluorine Chemistry, Ojima, I.; McCarthy, J. R.; Welch, J. T. Eds., ACS Books, American Chemical Society, Washington, D.C., Chapter 2, 1996; For most recent publications see: Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print, 58; Tetrahedron 1996, 52, 1-330.
    • (1996) Tetrahedron , vol.52 , pp. 1-330
  • 23
    • 0342829735 scopus 로고    scopus 로고
    • note
    • 2 derivatives were rather inert toward the addition reactions.
  • 24
    • 0342829729 scopus 로고    scopus 로고
    • note
    • 3), 5.51 (1H, d, α-CH), 5.92 (1H, m, β-CH), 7.07, 7.50 (4H, AB, J = 9.0 Hz, ArH).
  • 25
    • 0343264617 scopus 로고    scopus 로고
    • note
    • -3. Diffraction data were measured on an Siemens P4-PC diffractometer; radiation MoKα (λ = 0.71073 Å); temperature 289 K. Full crystallographic data have been deposited with the Cambridge Crystallographic Data Center and are available on request from L.V.M.
  • 26
    • 84981828672 scopus 로고
    • The (2S,3R)-configuration of the amino acid residue in complex 4, a consequence of the Cahn-Ingold-Prelog priority, is stereochemically equivalent to the (2S,3S)-configuration in the hydrocarbon analogs; Cahn, R.S.; Ingold, C.; Prelog, V. Angew. Chem. Int. Ed. Engl., 1966, 5, 385.
    • (1966) Angew. Chem. Int. Ed. Engl. , vol.5 , pp. 385
    • Cahn, R.S.1    Ingold, C.2    Prelog, V.3
  • 27
    • 0001797240 scopus 로고
    • Some effects of lithium salts, of strong bases, and of the cosolvent DMPU in peptide chemistry, and elsewhere
    • Ernst, B.; Leumann, C. Eds., Verlag Helvetica Chimica Acta: Basel, VCH: Weinheim
    • Seebach, D.; Beck, A. K.; Studer, A. "Some Effects of Lithium Salts, of Strong Bases, and of the Cosolvent DMPU in Peptide Chemistry, and Elsewhere" in Modern Synthetic Methods 1995, Vol. 7, Ernst, B.; Leumann, C. Eds., Verlag Helvetica Chimica Acta: Basel, VCH: Weinheim, 1995, 1-178.
    • (1995) Modern Synthetic Methods 1995 , vol.7 , pp. 1-178
    • Seebach, D.1    Beck, A.K.2    Studer, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.