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

Tetrahedron Letters

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

  Soloshonok, Vadim A ^a   Avilov, Dimitry V ^b   Kukhar, Valery P ^b   Van Meervelt, Luc ^c   Mischenko, Nikolai ^c  

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

^b INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

^c UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; THERMODYNAMICS;

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

References (28)

1. 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
2. (b) Duthaler, R. P. Tetrahedron 1994, 50, 1539; (β-amino acids)
3. (c) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3;
4. (d) Cole, D. C. Tetrahedron 1994, 50, 9517;
5. (e) Enantioselective Synthesis of β-Amino Acids, Juaristi, E. Ed., VCH Publishers, INC.: N.Y., 1997.
6. For a recent report on erythro-stereoselective transition metal-catalyzed aza-aldol reactions of methyl isocyanoacetate see: Hayashi, T.; Kishi, E.; Soloshonok, V.A.; Uozumi, Y. Tetrahedron Letters 1996, 37, 4969.
7. (a) Barrett, G. C., Ed. Chemistry and Biochemistry of the Amino Acids; Chapman and Hall: London, 1985;
8. (b) Greenstein, J. P.; Wintz, M. Chemistry of the Amino Acids; Robert E. Krieger: FL, 1984.
9. (a) Fluorine-Containing Amino Acids. Synthesis and Properties. Kukhar, V. P.; Soloshonok, V. A., Eds. Wiley: Chichester, 1995;
10. (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;
11. (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.
12. (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.
13. (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.
14. (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.
15. (a) Martin, J. H.; Hausmann, W. K. J. Am. Chem. Soc. 1960, 82, 2079.
16. (b) Fujino, M.; Inoue, M.; Ueyanagi, J.; Miyake, A. Bull. Chem. Soc. Jap. 1965, 38, 515.
17. (c) Bodanszky, A. A.; Bodanszky, M. J. Antibiot. 1970, 23 149.
18. (d) Morimoto, K.; Shimada, N.; Naganawa, H.; Takita, T.; Umezawa, H. J. Antibiot. 1981, 34, 1613.
19. (e) Shiroza, T.; Ebisawa, N.; Furihata, K.; Endo, T.; Seto, H.; Otake, N. Agric. Biol. Chem. 1982, 46, 865.
20. (f) Uehida, I.; Shigematsu, N.; Ezaki, M.; Hashimoto, M. Chem. Pharm. Bull. 1985, 33, 3053.
21. Soloshonok, V. A. "Asymmetric Aldol Reactions of Fluoro-Carbonyl Compounds" in EPC-Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets, Soloshonok, V. A. Ed., Wiley: Chichester, scheduled to appear in 1997.
22. Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis; John Wiley: London, 1991.
23. 2 derivatives were rather inert toward the addition reactions.
24. 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. -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. 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.
27. 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.
28. Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron 1996, 52, 12433.