Biomimetic Transamination of α-Alkyl β-Keto Carboxylic Esters. Chemoenzymatic Approach to the Stereochemically Defined α-Alkyl β-Fluoroalkyl β-Amino Acids

Journal of Organic Chemistry

Volumn 63, Issue 6, 1998, Pages 1878-1884

  Soloshonok, Vadim A ^a   Soloshonok, Irina V ^a   Kukhar, Valery P ^b   Svedas, Vytas K ^c  

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

^b INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

^c MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001534452     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971777m     Document Type: Article

References (123)

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69. For general discussion of biological activity and importance of fluorinated amino compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; American Chemical Society: Washington, D.C., 1991. (c) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Eds.; Kodansha LTD: Tokyo, Elsevier: Amsterdam - New York Oxford, 1982. (d) Sieler, M.; Jung, M. J.; Koch-Waser. EnzymeActivated Irreversible Inhibitors; Elsevier: Amsterdam, 1978. (e) Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994. (f) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (g) Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, D.C., 1996. For most recent publications see: (h) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print No. 58. Tetrahedron 1996, 52, 1-330.
70. For general discussion of biological activity and importance of fluorinated amino compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; American Chemical Society: Washington, D.C., 1991. (c) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Eds.; Kodansha LTD: Tokyo, Elsevier: Amsterdam - New York Oxford, 1982. (d) Sieler, M.; Jung, M. J.; Koch-Waser. EnzymeActivated Irreversible Inhibitors; Elsevier: Amsterdam, 1978. (e) Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994. (f) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (g) Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, D.C., 1996. For most recent publications see: (h) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print No. 58. Tetrahedron 1996, 52, 1-330.
71. For general discussion of biological activity and importance of fluorinated amino compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; American Chemical Society: Washington, D.C., 1991. (c) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Eds.; Kodansha LTD: Tokyo, Elsevier: Amsterdam - New York Oxford, 1982. (d) Sieler, M.; Jung, M. J.; Koch-Waser. EnzymeActivated Irreversible Inhibitors; Elsevier: Amsterdam, 1978. (e) Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994. (f) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (g) Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, D.C., 1996. For most recent publications see: (h) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print No. 58. Tetrahedron 1996, 52, 1-330.
72. For general discussion of biological activity and importance of fluorinated amino compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; American Chemical Society: Washington, D.C., 1991. (c) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Eds.; Kodansha LTD: Tokyo, Elsevier: Amsterdam - New York Oxford, 1982. (d) Sieler, M.; Jung, M. J.; Koch-Waser. EnzymeActivated Irreversible Inhibitors; Elsevier: Amsterdam, 1978. (e) Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994. (f) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (g) Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, D.C., 1996. For most recent publications see: (h) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print No. 58. Tetrahedron 1996, 52, 1-330.
73. For general discussion of biological activity and importance of fluorinated amino compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; American Chemical Society: Washington, D.C., 1991. (c) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Eds.; Kodansha LTD: Tokyo, Elsevier: Amsterdam - New York Oxford, 1982. (d) Sieler, M.; Jung, M. J.; Koch-Waser. EnzymeActivated Irreversible Inhibitors; Elsevier: Amsterdam, 1978. (e) Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994. (f) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (g) Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, D.C., 1996. For most recent publications see: (h) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print No. 58. Tetrahedron 1996, 52, 1-330.
74. For general discussion of biological activity and importance of fluorinated amino compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; American Chemical Society: Washington, D.C., 1991. (c) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Eds.; Kodansha LTD: Tokyo, Elsevier: Amsterdam - New York Oxford, 1982. (d) Sieler, M.; Jung, M. J.; Koch-Waser. EnzymeActivated Irreversible Inhibitors; Elsevier: Amsterdam, 1978. (e) Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994. (f) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (g) Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, D.C., 1996. For most recent publications see: (h) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print No. 58. Tetrahedron 1996, 52, 1-330.
75. For general discussion of biological activity and importance of fluorinated amino compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; American Chemical Society: Washington, D.C., 1991. (c) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Eds.; Kodansha LTD: Tokyo, Elsevier: Amsterdam - New York Oxford, 1982. (d) Sieler, M.; Jung, M. J.; Koch-Waser. EnzymeActivated Irreversible Inhibitors; Elsevier: Amsterdam, 1978. (e) Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994. (f) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (g) Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, D.C., 1996. For most recent publications see: (h) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print No. 58. Tetrahedron 1996, 52, 1-330.
76. For general discussion of biological activity and importance of fluorinated amino compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; American Chemical Society: Washington, D.C., 1991. (c) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Eds.; Kodansha LTD: Tokyo, Elsevier: Amsterdam - New York Oxford, 1982. (d) Sieler, M.; Jung, M. J.; Koch-Waser. EnzymeActivated Irreversible Inhibitors; Elsevier: Amsterdam, 1978. (e) Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994. (f) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (g) Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, D.C., 1996. For most recent publications see: (h) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print No. 58. Tetrahedron 1996, 52, 1-330.
77. (a) Snell, E. E. In Chemical and Biological Aspects of Pyridoxal Catalysis; Fasella, P. M., Braunstein, A. E., Rossi-Fanelli, A., Eds.; Macmillan: New York, 1963,
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79. In this condensation, apart from the (Z)-enamine 1a the corresponding N-benzyl-3-(N-benzylamino)-4,4,4-trifluorocrotonamide is also obtained as a minor reaction product.
80. Steric bulk and stereochemical behavior of the trifluoromethyl group is still a controversial issue. For recent papers and reviews highlighting the unique steric properties of the trifluoromethyl group see: (a) Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed., Wiley: Chichester, scheduled to appear in April 1998. (b) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; pp 57-88. (c) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (d) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron 1996, 52, 12433. (e) Soloshonok, V. A.; Avilov, D. V.; Kacharov, A. D.; Hayashi, T. Tetrahedron Lett. 1996, 37, 7845. (f) Bravo, P.; Farina, A.; Kukhar, V. P.; Markovsky, A. L.; Meille, S. V.; Soloshonok, V. A.; Sorochinsky, A. E.; Viani, F.; Zanda, M.; Zappala, C. J. Org. Chem. 1997, 62, 3424. (g) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem. 1997, 62, 3470. (h) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4671. (i) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4903.
81. Steric bulk and stereochemical behavior of the trifluoromethyl group is still a controversial issue. For recent papers and reviews highlighting the unique steric properties of the trifluoromethyl group see: (a) Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed., Wiley: Chichester, scheduled to appear in April 1998. (b) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; pp 57-88. (c) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (d) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron 1996, 52, 12433. (e) Soloshonok, V. A.; Avilov, D. V.; Kacharov, A. D.; Hayashi, T. Tetrahedron Lett. 1996, 37, 7845. (f) Bravo, P.; Farina, A.; Kukhar, V. P.; Markovsky, A. L.; Meille, S. V.; Soloshonok, V. A.; Sorochinsky, A. E.; Viani, F.; Zanda, M.; Zappala, C. J. Org. Chem. 1997, 62, 3424. (g) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem. 1997, 62, 3470. (h) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4671. (i) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4903.
82. Steric bulk and stereochemical behavior of the trifluoromethyl group is still a controversial issue. For recent papers and reviews highlighting the unique steric properties of the trifluoromethyl group see: (a) Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed., Wiley: Chichester, scheduled to appear in April 1998. (b) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; pp 57-88. (c) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (d) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron 1996, 52, 12433. (e) Soloshonok, V. A.; Avilov, D. V.; Kacharov, A. D.; Hayashi, T. Tetrahedron Lett. 1996, 37, 7845. (f) Bravo, P.; Farina, A.; Kukhar, V. P.; Markovsky, A. L.; Meille, S. V.; Soloshonok, V. A.; Sorochinsky, A. E.; Viani, F.; Zanda, M.; Zappala, C. J. Org. Chem. 1997, 62, 3424. (g) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem. 1997, 62, 3470. (h) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4671. (i) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4903.
83. Steric bulk and stereochemical behavior of the trifluoromethyl group is still a controversial issue. For recent papers and reviews highlighting the unique steric properties of the trifluoromethyl group see: (a) Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed., Wiley: Chichester, scheduled to appear in April 1998. (b) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; pp 57-88. (c) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (d) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron 1996, 52, 12433. (e) Soloshonok, V. A.; Avilov, D. V.; Kacharov, A. D.; Hayashi, T. Tetrahedron Lett. 1996, 37, 7845. (f) Bravo, P.; Farina, A.; Kukhar, V. P.; Markovsky, A. L.; Meille, S. V.; Soloshonok, V. A.; Sorochinsky, A. E.; Viani, F.; Zanda, M.; Zappala, C. J. Org. Chem. 1997, 62, 3424. (g) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem. 1997, 62, 3470. (h) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4671. (i) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4903.
84. Steric bulk and stereochemical behavior of the trifluoromethyl group is still a controversial issue. For recent papers and reviews highlighting the unique steric properties of the trifluoromethyl group see: (a) Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed., Wiley: Chichester, scheduled to appear in April 1998. (b) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; pp 57-88. (c) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (d) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron 1996, 52, 12433. (e) Soloshonok, V. A.; Avilov, D. V.; Kacharov, A. D.; Hayashi, T. Tetrahedron Lett. 1996, 37, 7845. (f) Bravo, P.; Farina, A.; Kukhar, V. P.; Markovsky, A. L.; Meille, S. V.; Soloshonok, V. A.; Sorochinsky, A. E.; Viani, F.; Zanda, M.; Zappala, C. J. Org. Chem. 1997, 62, 3424. (g) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem. 1997, 62, 3470. (h) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4671. (i) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4903.
85. Steric bulk and stereochemical behavior of the trifluoromethyl group is still a controversial issue. For recent papers and reviews highlighting the unique steric properties of the trifluoromethyl group see: (a) Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed., Wiley: Chichester, scheduled to appear in April 1998. (b) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; pp 57-88. (c) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (d) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron 1996, 52, 12433. (e) Soloshonok, V. A.; Avilov, D. V.; Kacharov, A. D.; Hayashi, T. Tetrahedron Lett. 1996, 37, 7845. (f) Bravo, P.; Farina, A.; Kukhar, V. P.; Markovsky, A. L.; Meille, S. V.; Soloshonok, V. A.; Sorochinsky, A. E.; Viani, F.; Zanda, M.; Zappala, C. J. Org. Chem. 1997, 62, 3424. (g) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem. 1997, 62, 3470. (h) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4671. (i) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4903.
86. Steric bulk and stereochemical behavior of the trifluoromethyl group is still a controversial issue. For recent papers and reviews highlighting the unique steric properties of the trifluoromethyl group see: (a) Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed., Wiley: Chichester, scheduled to appear in April 1998. (b) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; pp 57-88. (c) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (d) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron 1996, 52, 12433. (e) Soloshonok, V. A.; Avilov, D. V.; Kacharov, A. D.; Hayashi, T. Tetrahedron Lett. 1996, 37, 7845. (f) Bravo, P.; Farina, A.; Kukhar, V. P.; Markovsky, A. L.; Meille, S. V.; Soloshonok, V. A.; Sorochinsky, A. E.; Viani, F.; Zanda, M.; Zappala, C. J. Org. Chem. 1997, 62, 3424. (g) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem. 1997, 62, 3470. (h) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4671. (i) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4903.
87. Steric bulk and stereochemical behavior of the trifluoromethyl group is still a controversial issue. For recent papers and reviews highlighting the unique steric properties of the trifluoromethyl group see: (a) Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed., Wiley: Chichester, scheduled to appear in April 1998. (b) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; pp 57-88. (c) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (d) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron 1996, 52, 12433. (e) Soloshonok, V. A.; Avilov, D. V.; Kacharov, A. D.; Hayashi, T. Tetrahedron Lett. 1996, 37, 7845. (f) Bravo, P.; Farina, A.; Kukhar, V. P.; Markovsky, A. L.; Meille, S. V.; Soloshonok, V. A.; Sorochinsky, A. E.; Viani, F.; Zanda, M.; Zappala, C. J. Org. Chem. 1997, 62, 3424. (g) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem. 1997, 62, 3470. (h) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4671. (i) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4903.
88. Steric bulk and stereochemical behavior of the trifluoromethyl group is still a controversial issue. For recent papers and reviews highlighting the unique steric properties of the trifluoromethyl group see: (a) Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed., Wiley: Chichester, scheduled to appear in April 1998. (b) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; pp 57-88. (c) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (d) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron 1996, 52, 12433. (e) Soloshonok, V. A.; Avilov, D. V.; Kacharov, A. D.; Hayashi, T. Tetrahedron Lett. 1996, 37, 7845. (f) Bravo, P.; Farina, A.; Kukhar, V. P.; Markovsky, A. L.; Meille, S. V.; Soloshonok, V. A.; Sorochinsky, A. E.; Viani, F.; Zanda, M.; Zappala, C. J. Org. Chem. 1997, 62, 3424. (g) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem. 1997, 62, 3470. (h) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4671. (i) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4903.
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