Synthesis and reactivity of enantiomerically pure 2-fluoromethyl-2-(1'- p-tolylsulfinyl) alkyl oxiranes

Tetrahedron

Volumn 54, Issue 39, 1998, Pages 11825-11840

  Arnone, Alberto ^a   Bravo, Pierfrancesco ^a   Frigerio, Massimo ^a   Viani, Fiorenza ^a   Soloshonok, Vadim 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

ETHYLENE OXIDE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DESULFURIZATION; DIASTEREOISOMER; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032563998     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)83042-1     Document Type: Article

References (39)

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2. For general reviews on fluoro-organic compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Biomedicinal Aspects of Fluorine Chemistry; 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. For recent publications see: (g) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print # 58; Tetrahedron 1996, 52, 1-330.
3. For general reviews on fluoro-organic compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Biomedicinal Aspects of Fluorine Chemistry; 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. For recent publications see: (g) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print # 58; Tetrahedron 1996, 52, 1-330.
4. For general reviews on fluoro-organic compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Biomedicinal Aspects of Fluorine Chemistry; 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. For recent publications see: (g) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print # 58; Tetrahedron 1996, 52, 1-330.
5. For general reviews on fluoro-organic compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Biomedicinal Aspects of Fluorine Chemistry; 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. For recent publications see: (g) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print # 58; Tetrahedron 1996, 52, 1-330.
6. For general reviews on fluoro-organic compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Biomedicinal Aspects of Fluorine Chemistry; 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. For recent publications see: (g) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print # 58; Tetrahedron 1996, 52, 1-330.
7. For general reviews on fluoro-organic compounds see: (a) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991. (b) Biomedicinal Aspects of Fluorine Chemistry; 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. For recent publications see: (g) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V. A., Eds.; Tetrahedron Symposium-in-Print # 58; Tetrahedron 1996, 52, 1-330.
8. (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.
9. (b) Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed.; Wiley: Chichester, scheduled to appear in 1998.
10. For discussion on Stereochemical properties of fluorine substituents see: (a) ref. 3 (b). (b) 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. (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.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (f) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (g) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (h) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
11. For discussion on Stereochemical properties of fluorine substituents see: (a) ref. 3 (b). (b) 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. (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.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (f) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (g) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (h) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
12. For discussion on Stereochemical properties of fluorine substituents see: (a) ref. 3 (b). (b) 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. (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.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (f) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (g) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (h) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
13. For discussion on Stereochemical properties of fluorine substituents see: (a) ref. 3 (b). (b) 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. (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.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (f) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (g) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (h) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
14. For discussion on Stereochemical properties of fluorine substituents see: (a) ref. 3 (b). (b) 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. (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.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (f) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (g) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (h) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
15. For discussion on Stereochemical properties of fluorine substituents see: (a) ref. 3 (b). (b) 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. (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.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (f) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (g) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (h) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
16. For discussion on Stereochemical properties of fluorine substituents see: (a) ref. 3 (b). (b) 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. (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.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem., 1997, 62, 3470. (f) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4671. (g) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Letters, 1997, 38, 4903. (h) Wipf, P.; Jung, J.-K. Angew. Chem. Int. Ed. Engl. 1997, 36, 764. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem., 1997, 62, 8288.
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