Highly diastereoselective methylene transfer from diazomethane to the carbonyl of β-keto sulfoxides. A general approach to synthetically versatile fluorine-containing chiral building blocks

Tetrahedron

Volumn 54, Issue 39, 1998, Pages 11841-11860

  Arnone, Alberto ^a   Bravo, Pierfrancesco ^a   Frigerio, Massimo ^a   Viani, Fiorenza ^a   Soloshonok, Vadini A ^b  

^a POLITECNICO DI MILANO   (Italy)

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

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DESULFURIZATION; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

TRIFLUORO;

EID: 0032564004     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)83043-3     Document Type: Article

References (56)

1. For general reviews: Catalytic Asymmetric Synthesis, Ojima, I. Ed. VCH Publishers, New York, 1993.
2. (a) Enantiocontrolled Synthesis of Fluoro-Organic Compounds, Tetrahedron Asymmetry Special Issue, Guest Editors: T. Hayashi and V. A. Soloshonok, Tetrahedron: Asymmetry, 1994, 5 (6), 955-1126.
3. (b) Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed.; Wiley: Chichester, scheduled to appear in 1998.
4. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
5. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
6. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
7. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
8. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
9. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
10. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
11. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
12. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
13. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
14. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
15. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
16. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
17. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
18. For discussions on Stereochemical properties of fluorine substituents and an inversion of Stereochemical outcome of asymmetric reactions provided by fluorine see: (a) Soloshonok, V. A., Kukhar', V. P.; Galushko, S. V.; Svistunova, N.Yu.; Avilov, D.V.; Kuz'mina, N.A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky, A. P.; Belokon', Yu. N. J. Chem. Soc. Perkin Trans. 1 1993, 3143. (b) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725. (c) Iseki, K.; Oishi, S.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 8147. (d) Soloshonok, V. A.; Hayashi, T.; Ishihara, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061. (f) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron : Asymmetry 1994, 5, 1075. (g) Iseki, K.; Oishi, S.; Kobayashi, Y. Chem. Lett. 1994, 1135. (h) Edwards, F. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994, pp. 501-541. (i) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99. (j) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron, 1996, 52, 12433. (k) Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (l) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (m) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (n) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (o) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
19. Ono, T. "Asymmetric Oxidation of Fluoro-Olefins". In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Chapter 9, Soloshonok, V. A., Ed.; Wiley: Chichester, scheduled to appear in 1998.
20. For general reviews on synthesis and biological relevance of fluoro-organic compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Organofluorine Compounds in Medicinal Chemistry and Biomedicinal Applications; Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (c) Resnati, G. Tetrahedron 1993, 49, 9385. (d) Fluorine-Containing Amino Acids: Synthesis and Properties; Kukhar, V.P.; Soloshonok, V.A., Eds.; Wiley: Chichester, 1994. (e) Organofluorine Chemistry: Principles and Commercial Applications, Banks, R.E.; Smart, B.E.; Tatlow, J.C., Eds.; Plenum Press: New York, 1994. (f) Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J.R.; Welch, J.T., Eds.; ACS Books, American Chemical Society: Washington, D.C., 1996. (g) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V.A., Eds.; Tetrahedron Symposium-in-Print # 58; Tetrahedron 1996, 52, 1-330.
21. For general reviews on synthesis and biological relevance of fluoro-organic compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Organofluorine Compounds in Medicinal Chemistry and Biomedicinal Applications; Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (c) Resnati, G. Tetrahedron 1993, 49, 9385. (d) Fluorine-Containing Amino Acids: Synthesis and Properties; Kukhar, V.P.; Soloshonok, V.A., Eds.; Wiley: Chichester, 1994. (e) Organofluorine Chemistry: Principles and Commercial Applications, Banks, R.E.; Smart, B.E.; Tatlow, J.C., Eds.; Plenum Press: New York, 1994. (f) Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J.R.; Welch, J.T., Eds.; ACS Books, American Chemical Society: Washington, D.C., 1996. (g) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V.A., Eds.; Tetrahedron Symposium-in-Print # 58; Tetrahedron 1996, 52, 1-330.
22. For general reviews on synthesis and biological relevance of fluoro-organic compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Organofluorine Compounds in Medicinal Chemistry and Biomedicinal Applications; Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (c) Resnati, G. Tetrahedron 1993, 49, 9385. (d) Fluorine-Containing Amino Acids: Synthesis and Properties; Kukhar, V.P.; Soloshonok, V.A., Eds.; Wiley: Chichester, 1994. (e) Organofluorine Chemistry: Principles and Commercial Applications, Banks, R.E.; Smart, B.E.; Tatlow, J.C., Eds.; Plenum Press: New York, 1994. (f) Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J.R.; Welch, J.T., Eds.; ACS Books, American Chemical Society: Washington, D.C., 1996. (g) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V.A., Eds.; Tetrahedron Symposium-in-Print # 58; Tetrahedron 1996, 52, 1-330.
23. For general reviews on synthesis and biological relevance of fluoro-organic compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Organofluorine Compounds in Medicinal Chemistry and Biomedicinal Applications; Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (c) Resnati, G. Tetrahedron 1993, 49, 9385. (d) Fluorine-Containing Amino Acids: Synthesis and Properties; Kukhar, V.P.; Soloshonok, V.A., Eds.; Wiley: Chichester, 1994. (e) Organofluorine Chemistry: Principles and Commercial Applications, Banks, R.E.; Smart, B.E.; Tatlow, J.C., Eds.; Plenum Press: New York, 1994. (f) Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J.R.; Welch, J.T., Eds.; ACS Books, American Chemical Society: Washington, D.C., 1996. (g) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V.A., Eds.; Tetrahedron Symposium-in-Print # 58; Tetrahedron 1996, 52, 1-330.
24. For general reviews on synthesis and biological relevance of fluoro-organic compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Organofluorine Compounds in Medicinal Chemistry and Biomedicinal Applications; Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (c) Resnati, G. Tetrahedron 1993, 49, 9385. (d) Fluorine-Containing Amino Acids: Synthesis and Properties; Kukhar, V.P.; Soloshonok, V.A., Eds.; Wiley: Chichester, 1994. (e) Organofluorine Chemistry: Principles and Commercial Applications, Banks, R.E.; Smart, B.E.; Tatlow, J.C., Eds.; Plenum Press: New York, 1994. (f) Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J.R.; Welch, J.T., Eds.; ACS Books, American Chemical Society: Washington, D.C., 1996. (g) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V.A., Eds.; Tetrahedron Symposium-in-Print # 58; Tetrahedron 1996, 52, 1-330.
25. For general reviews on synthesis and biological relevance of fluoro-organic compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Organofluorine Compounds in Medicinal Chemistry and Biomedicinal Applications; Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (c) Resnati, G. Tetrahedron 1993, 49, 9385. (d) Fluorine-Containing Amino Acids: Synthesis and Properties; Kukhar, V.P.; Soloshonok, V.A., Eds.; Wiley: Chichester, 1994. (e) Organofluorine Chemistry: Principles and Commercial Applications, Banks, R.E.; Smart, B.E.; Tatlow, J.C., Eds.; Plenum Press: New York, 1994. (f) Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J.R.; Welch, J.T., Eds.; ACS Books, American Chemical Society: Washington, D.C., 1996. (g) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V.A., Eds.; Tetrahedron Symposium-in-Print # 58; Tetrahedron 1996, 52, 1-330.
26. For general reviews on synthesis and biological relevance of fluoro-organic compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Organofluorine Compounds in Medicinal Chemistry and Biomedicinal Applications; Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (c) Resnati, G. Tetrahedron 1993, 49, 9385. (d) Fluorine-Containing Amino Acids: Synthesis and Properties; Kukhar, V.P.; Soloshonok, V.A., Eds.; Wiley: Chichester, 1994. (e) Organofluorine Chemistry: Principles and Commercial Applications, Banks, R.E.; Smart, B.E.; Tatlow, J.C., Eds.; Plenum Press: New York, 1994. (f) Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J.R.; Welch, J.T., Eds.; ACS Books, American Chemical Society: Washington, D.C., 1996. (g) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V.A., Eds.; Tetrahedron Symposium-in-Print # 58; Tetrahedron 1996, 52, 1-330.
27. Takahashi, O.; Furuhashi, K.; Fukumasa, M.; Hirai, T. Tetrahedron Letters, 1990, 31, 7031.
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30. Katagiri, T. "Synthesis of Stereochemically Defined Trifluoromethyl-Containing Compounds through (S)-3,3,3-Trifluoropropene Oxide". In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Chapter 5, Soloshonok, V. A., Ed.; Wiley: Chichester, scheduled to appear in 1998.
31. Bravo, P.; Zanda, M. "Asymmetric Synthesis of Fluoro-Organic Compounds via Chiral Sulfoxide Chemistry". In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Chapter 4, Soloshonok, V. A., Ed.; Wiley: Chichester, scheduled to appear in 1998.
32. (a) Kukhar, V. P.; Resnati, G.; Soloshonok, V. A. "Asymmetric Synthesis of Fluorine-containing Amino Acids". In Fluorine-Containing Amino Acids. Synthesis and properties. Kukhar', V. P.; Soloshonok, V. A., Eds.; John Wiley and Sons Ltd.: Chichester, 1995; Chapter 5.
33. (b) 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., 1996; Chapter 2.
34. (c) Soloshonok, V. A. "Biocatalytic Entry to Enantiomerically Pure β-Amino Acids". In Enantioselective Synthesis of β-Amino Acids Juaristi, E. Ed.; Wiley-VCH Publisher: New York, Chapter 21, 1997.
35. (d) Soloshonok, V. A. "Asymmetric Aldol Reactions of Fluoro-Carbonyl Compounds". In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets, Soloshonok, V. A. Ed.; Wiley: Chichester, scheduled to appear in April 1998.
36. See for example: (a) Methoden Der Organischen Chemie, Houben-Weyl; Müller, E., Ed.; G. Thieme Verlag: Stuttgart, 1968; Vol. X/4, Prt IV, p 712. (b) Methoden Der Organischen Chemie, Houben-Weyl; Müller, E., Ed.; G. Thieme Verlag: Stuttgart, 1976; Vol. VII/2b, Prt II, p 1855. (b) The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Wiley: NY, 1978; pp575 and 598. (c) Advanced Organic Chemistry; March, J.; Wiley: NY, 1985; pp 866 and 976.
37. See for example: (a) Methoden Der Organischen Chemie, Houben-Weyl; Müller, E., Ed.; G. Thieme Verlag: Stuttgart, 1968; Vol. X/4, Prt IV, p 712. (b) Methoden Der Organischen Chemie, Houben-Weyl; Müller, E., Ed.; G. Thieme Verlag: Stuttgart, 1976; Vol. VII/2b, Prt II, p 1855. (b) The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Wiley: NY, 1978; pp575 and 598. (c) Advanced Organic Chemistry; March, J.; Wiley: NY, 1985; pp 866 and 976.
38. See for example: (a) Methoden Der Organischen Chemie, Houben-Weyl; Müller, E., Ed.; G. Thieme Verlag: Stuttgart, 1968; Vol. X/4, Prt IV, p 712. (b) Methoden Der Organischen Chemie, Houben-Weyl; Müller, E., Ed.; G. Thieme Verlag: Stuttgart, 1976; Vol. VII/2b, Prt II, p 1855. (b) The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Wiley: NY, 1978; pp575 and 598. (c) Advanced Organic Chemistry; March, J.; Wiley: NY, 1985; pp 866 and 976.
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