Highly Enantioselective Transfer of Chirality from a Less to a More Configurationally Unstable Stereogenie Center. A Practical Asymmetric Synthesis of (Fluoroalkyl) amines via Biomimetic Transamination

Journal of Organic Chemistry

Volumn 62, Issue 10, 1997, Pages 3030-3031

  Soloshonok, Vadim A ^a   Ono, Taizo ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ORGANOFLUORINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030916859     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970425c     Document Type: Article

References (21)

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3. (c) Soloshonok, V. A.; Ono, T. Tetrahedron 1996, 52, 14701 and other references on PSR cited therein.
4. For a general discussion of the biological activity and importance of fluorinated amino compounds see the following monographs: (a) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (b) Fluorine-Containing Amino Acids: Synthesis and Properties; Kukhar, V. P., Soloshonok, V. A., Eds.; Wiley: Chichester, 1994. (c) Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, D.C., 1996. For the most recent publications see: (d) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G., Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print No. 58; Tetrahedron 1996, 52, 1-330.
5. For a general discussion of the biological activity and importance of fluorinated amino compounds see the following monographs: (a) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (b) Fluorine-Containing Amino Acids: Synthesis and Properties; Kukhar, V. P., Soloshonok, V. A., Eds.; Wiley: Chichester, 1994. (c) Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, D.C., 1996. For the most recent publications see: (d) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G., Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print No. 58; Tetrahedron 1996, 52, 1-330.
6. For a general discussion of the biological activity and importance of fluorinated amino compounds see the following monographs: (a) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (b) Fluorine-Containing Amino Acids: Synthesis and Properties; Kukhar, V. P., Soloshonok, V. A., Eds.; Wiley: Chichester, 1994. (c) Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, D.C., 1996. For the most recent publications see: (d) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G., Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print No. 58; Tetrahedron 1996, 52, 1-330.
7. For a general discussion of the biological activity and importance of fluorinated amino compounds see the following monographs: (a) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (b) Fluorine-Containing Amino Acids: Synthesis and Properties; Kukhar, V. P., Soloshonok, V. A., Eds.; Wiley: Chichester, 1994. (c) Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, D.C., 1996. For the most recent publications see: (d) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G., Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print No. 58; Tetrahedron 1996, 52, 1-330.
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18. We have shown that forced reaction conditions and strong bases cause dehydrofluorination of Schiff bases of type 4; see refs 1b and 7.
19. It clearly follows from the fact that, for instance, in boiling TEA product 4a easily undergoes racemization while the starting 3a remains stereochemically intact; see Table 1.
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21. (a) Asymmetric reduction: Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1977, 42, 2436. (b) Classical resolution: Wang, Y.; Mosher, H. S. Tetrahedron Lett. 1991, 32, 987.