Highly diastereoselective asymmetric aldol reactions of chiral Ni(II)-complex of glycine with alkyl trifluoromethyl ketones

Tetrahedron Asymmetry

Volumn 7, Issue 6, 1996, Pages 1547-1550

  Soloshonok, Vadim A ^a,b   Avilov, Dimitry V ^b   Kukhar', Valery P ^b  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; BENZOPHENONE DERIVATIVE; GLYCINE; KETONE DERIVATIVE; NICKEL; SCHIFF BASE; SERINE DERIVATIVE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; PRIORITY JOURNAL; SYNTHESIS;

EID: 0029883406     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00177-2     Document Type: Article

References (23)

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9. Apart from their own biological activity, β,β-disubstituted-β-hydroxy acids, which exert defined conformational constraints, could be of interest in the de novo design of peptides and proteins with specific conformational properties and biological functions. Peptide Chemistry: Design and Synthesis of Peptides, Conformational Analysis and Biological Functions; Hruby V. J.; Schwyzer, R., Eds.; Tetrahedron-Symposia-in-Print, 31; Tetrahedron 1988, 44, 661.
10. Apart from their own biological activity, β,β-disubstituted-β-hydroxy acids, which exert defined conformational constraints, could be of interest in the de novo design of peptides and proteins with specific conformational properties and biological functions. Peptide Chemistry: Design and Synthesis of Peptides, Conformational Analysis and Biological Functions; Hruby V. J.; Schwyzer, R., Eds.; Tetrahedron-Symposia-in-Print, 31; Tetrahedron 1988, 44, 661.
11. For general review on fluorine-containing amino acids see: Fluorine-Containing Amino Acids. Synthesis and Properties. Kukhar, V. P.; Soloshonok, V. A., Eds.; John Wiley and Sons Ltd, Chichester, 1994. 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.
12. For general review on fluorine-containing amino acids see: Fluorine-Containing Amino Acids. Synthesis and Properties. Kukhar, V. P.; Soloshonok, V. A., Eds.; John Wiley and Sons Ltd, Chichester, 1994. 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.
13. For general review on fluorine-containing amino acids see: Fluorine-Containing Amino Acids. Synthesis and Properties. Kukhar, V. P.; Soloshonok, V. A., Eds.; John Wiley and Sons Ltd, Chichester, 1994. 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.
14. In view of critical involvement of β-hydroxy amino acids in the biological activities of numerous naturally occurring peptide and glycopeptide antibiotics, application of β-(trifluoromethyl)-β-substituted-β-hydroxy amino acids as structural units for modification of these biological macromolecules might be promising. For recent stereoselective approaches to this class of amino acids see: (a) Sting, A. R.; Seebach, D. Tetrahedron 1996, 52, 279.
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17. (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Yu. T.; Raevsky, N. I.; Belokon', Yu. N. Tetrahedron: Asymmetry, 1995, 6, 1741.
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20. (2S,3S)-4,4,4-Trifluorothreonine and (2S,3S)-4,4-difluorothreonine were found to possess promising antitumour and antifungal activity. (a) Kitazume, T.; Lin, J. T.; Yamazaki, T. Tetrahedron: Asymmetry 1991, 2, 235.
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22. (2S,3S)-Configuration, a consequence of the Cahn-Ingold-Prelog priority, is stereochemically equivalent to the (2S,3R )-configuration in the hydrocarbon analogs; Cahn, R.S.; Ingold, C.; Prelog, V. Angew. Chem. Int. Ed. Engl., 1966, 5, 385.
23. 3).