Samarium(II) Iodide-Promoted Reactions of 2,3-Epoxycycloalkanone Hydrazones

Synlett

Volumn 1997, Issue 1, 1997, Pages 33-34

  Kang, Han Young ^a   Hong, Woo Sang ^a   Lee, Sang Hak ^a   Choi, Kyung Il ^b   Koh, Hun Yeong ^b  

^a Chungbuk National University   (South Korea)

^b Korea Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010406756     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-713     Document Type: Article

References (27)

1. For reviews see: (a) Natale, N. R. Org. Prep. Proc. Int. 1983, 15, 387-424. (b) Kagan, H. B.; Sasaki, M.; Collin, J. Tetrahedron. 1986, 42, 6573-6694. (c) Kagan, H. B.; Sasaki, M.; Collin, J. Pure Appl. Chem. 1988, 60, 1725-1730. (d) Molander, G. A. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R. Ed.; John Wiley & Sons: Chichester, 1989; Vol. 5, Chapter 8. (e) Inanaga, J.; Yamaguchi, M. In New Aspects of Organic Chemistry 1; Yoshida, Z.; Shiba, T.; Oshiro, Y. Eds.; VCH: New York, 1989; Chapter 4. (f) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (g) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (h) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (h) Molander G. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U. K., 1991; Vol. 1, Chapter 1.9. (i) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4. (j) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
2. For reviews see: (a) Natale, N. R. Org. Prep. Proc. Int. 1983, 15, 387-424. (b) Kagan, H. B.; Sasaki, M.; Collin, J. Tetrahedron. 1986, 42, 6573-6694. (c) Kagan, H. B.; Sasaki, M.; Collin, J. Pure Appl. Chem. 1988, 60, 1725-1730. (d) Molander, G. A. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R. Ed.; John Wiley & Sons: Chichester, 1989; Vol. 5, Chapter 8. (e) Inanaga, J.; Yamaguchi, M. In New Aspects of Organic Chemistry 1; Yoshida, Z.; Shiba, T.; Oshiro, Y. Eds.; VCH: New York, 1989; Chapter 4. (f) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (g) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (h) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (h) Molander G. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U. K., 1991; Vol. 1, Chapter 1.9. (i) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4. (j) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
3. For reviews see: (a) Natale, N. R. Org. Prep. Proc. Int. 1983, 15, 387-424. (b) Kagan, H. B.; Sasaki, M.; Collin, J. Tetrahedron. 1986, 42, 6573-6694. (c) Kagan, H. B.; Sasaki, M.; Collin, J. Pure Appl. Chem. 1988, 60, 1725-1730. (d) Molander, G. A. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R. Ed.; John Wiley & Sons: Chichester, 1989; Vol. 5, Chapter 8. (e) Inanaga, J.; Yamaguchi, M. In New Aspects of Organic Chemistry 1; Yoshida, Z.; Shiba, T.; Oshiro, Y. Eds.; VCH: New York, 1989; Chapter 4. (f) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (g) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (h) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (h) Molander G. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U. K., 1991; Vol. 1, Chapter 1.9. (i) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4. (j) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
4. For reviews see: (a) Natale, N. R. Org. Prep. Proc. Int. 1983, 15, 387-424. (b) Kagan, H. B.; Sasaki, M.; Collin, J. Tetrahedron. 1986, 42, 6573-6694. (c) Kagan, H. B.; Sasaki, M.; Collin, J. Pure Appl. Chem. 1988, 60, 1725-1730. (d) Molander, G. A. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R. Ed.; John Wiley & Sons: Chichester, 1989; Vol. 5, Chapter 8. (e) Inanaga, J.; Yamaguchi, M. In New Aspects of Organic Chemistry 1; Yoshida, Z.; Shiba, T.; Oshiro, Y. Eds.; VCH: New York, 1989; Chapter 4. (f) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (g) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (h) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (h) Molander G. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U. K., 1991; Vol. 1, Chapter 1.9. (i) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4. (j) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
5. For reviews see: (a) Natale, N. R. Org. Prep. Proc. Int. 1983, 15, 387-424. (b) Kagan, H. B.; Sasaki, M.; Collin, J. Tetrahedron. 1986, 42, 6573-6694. (c) Kagan, H. B.; Sasaki, M.; Collin, J. Pure Appl. Chem. 1988, 60, 1725-1730. (d) Molander, G. A. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R. Ed.; John Wiley & Sons: Chichester, 1989; Vol. 5, Chapter 8. (e) Inanaga, J.; Yamaguchi, M. In New Aspects of Organic Chemistry 1; Yoshida, Z.; Shiba, T.; Oshiro, Y. Eds.; VCH: New York, 1989; Chapter 4. (f) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (g) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (h) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (h) Molander G. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U. K., 1991; Vol. 1, Chapter 1.9. (i) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4. (j) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
6. For reviews see: (a) Natale, N. R. Org. Prep. Proc. Int. 1983, 15, 387-424. (b) Kagan, H. B.; Sasaki, M.; Collin, J. Tetrahedron. 1986, 42, 6573-6694. (c) Kagan, H. B.; Sasaki, M.; Collin, J. Pure Appl. Chem. 1988, 60, 1725-1730. (d) Molander, G. A. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R. Ed.; John Wiley & Sons: Chichester, 1989; Vol. 5, Chapter 8. (e) Inanaga, J.; Yamaguchi, M. In New Aspects of Organic Chemistry 1; Yoshida, Z.; Shiba, T.; Oshiro, Y. Eds.; VCH: New York, 1989; Chapter 4. (f) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (g) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (h) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (h) Molander G. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U. K., 1991; Vol. 1, Chapter 1.9. (i) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4. (j) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
7. For reviews see: (a) Natale, N. R. Org. Prep. Proc. Int. 1983, 15, 387-424. (b) Kagan, H. B.; Sasaki, M.; Collin, J. Tetrahedron. 1986, 42, 6573-6694. (c) Kagan, H. B.; Sasaki, M.; Collin, J. Pure Appl. Chem. 1988, 60, 1725-1730. (d) Molander, G. A. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R. Ed.; John Wiley & Sons: Chichester, 1989; Vol. 5, Chapter 8. (e) Inanaga, J.; Yamaguchi, M. In New Aspects of Organic Chemistry 1; Yoshida, Z.; Shiba, T.; Oshiro, Y. Eds.; VCH: New York, 1989; Chapter 4. (f) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (g) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (h) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (h) Molander G. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U. K., 1991; Vol. 1, Chapter 1.9. (i) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4. (j) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
8. For reviews see: (a) Natale, N. R. Org. Prep. Proc. Int. 1983, 15, 387-424. (b) Kagan, H. B.; Sasaki, M.; Collin, J. Tetrahedron. 1986, 42, 6573-6694. (c) Kagan, H. B.; Sasaki, M.; Collin, J. Pure Appl. Chem. 1988, 60, 1725-1730. (d) Molander, G. A. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R. Ed.; John Wiley & Sons: Chichester, 1989; Vol. 5, Chapter 8. (e) Inanaga, J.; Yamaguchi, M. In New Aspects of Organic Chemistry 1; Yoshida, Z.; Shiba, T.; Oshiro, Y. Eds.; VCH: New York, 1989; Chapter 4. (f) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (g) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (h) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (h) Molander G. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U. K., 1991; Vol. 1, Chapter 1.9. (i) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4. (j) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
9. For reviews see: (a) Natale, N. R. Org. Prep. Proc. Int. 1983, 15, 387-424. (b) Kagan, H. B.; Sasaki, M.; Collin, J. Tetrahedron. 1986, 42, 6573-6694. (c) Kagan, H. B.; Sasaki, M.; Collin, J. Pure Appl. Chem. 1988, 60, 1725-1730. (d) Molander, G. A. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R. Ed.; John Wiley & Sons: Chichester, 1989; Vol. 5, Chapter 8. (e) Inanaga, J.; Yamaguchi, M. In New Aspects of Organic Chemistry 1; Yoshida, Z.; Shiba, T.; Oshiro, Y. Eds.; VCH: New York, 1989; Chapter 4. (f) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (g) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (h) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (h) Molander G. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U. K., 1991; Vol. 1, Chapter 1.9. (i) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4. (j) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
10. For reviews see: (a) Natale, N. R. Org. Prep. Proc. Int. 1983, 15, 387-424. (b) Kagan, H. B.; Sasaki, M.; Collin, J. Tetrahedron. 1986, 42, 6573-6694. (c) Kagan, H. B.; Sasaki, M.; Collin, J. Pure Appl. Chem. 1988, 60, 1725-1730. (d) Molander, G. A. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R. Ed.; John Wiley & Sons: Chichester, 1989; Vol. 5, Chapter 8. (e) Inanaga, J.; Yamaguchi, M. In New Aspects of Organic Chemistry 1; Yoshida, Z.; Shiba, T.; Oshiro, Y. Eds.; VCH: New York, 1989; Chapter 4. (f) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (g) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (h) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (h) Molander G. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U. K., 1991; Vol. 1, Chapter 1.9. (i) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4. (j) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
11. For reviews see: (a) Natale, N. R. Org. Prep. Proc. Int. 1983, 15, 387-424. (b) Kagan, H. B.; Sasaki, M.; Collin, J. Tetrahedron. 1986, 42, 6573-6694. (c) Kagan, H. B.; Sasaki, M.; Collin, J. Pure Appl. Chem. 1988, 60, 1725-1730. (d) Molander, G. A. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R. Ed.; John Wiley & Sons: Chichester, 1989; Vol. 5, Chapter 8. (e) Inanaga, J.; Yamaguchi, M. In New Aspects of Organic Chemistry 1; Yoshida, Z.; Shiba, T.; Oshiro, Y. Eds.; VCH: New York, 1989; Chapter 4. (f) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (g) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (h) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (h) Molander G. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U. K., 1991; Vol. 1, Chapter 1.9. (i) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4. (j) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
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22. 4Cl solution was added. Usual workup and silica-gel chromatography provided 3-iodo-2-cylclohexen-1-ol (2) (21 mg, 35%) as an oil.
23. (a) Knochel, P.; Rao, C. J. Tetrahedron 1993, 49, 29-48.
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25. 3. The final R value was 0.0454 for 1622 (I>3σ(I)) reflections.
26. Mori, K.; Tamada, S.; Uchida, M.; Mizumachi, N.; Tachibana, Y.; Matsui, M. Tetrahedron 1978, 34, 1901-1903.
27. 3. See Studer, A.; Curran, D. P. Synlett 1996, 255-256.