Hybrid reagent of ammonium hydrogen fluoride and scandium triflate: Highly efficient catalyst for ring-opening fluorination of 2,3-epoxyalcohols

Chemistry Letters

Volumn 33, Issue 6, 2004, Pages 776-777

  Itoh, Yoshimitsu ^a   Jang, Sejin ^a,b   Ohba, Siho ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b Kyonboku University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM HYDROGEN FLUORIDE; FLUORIDE; SCANDIUM TRIFLATE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; FLUORINATION; REACTION ANALYSIS;

EID: 4444288487     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.776     Document Type: Article

References (35)

1. K. Mikami, Y. Itoh, and M. Yamanaka, Chem. Rev., 104, 1 (2004); Fine Chemical 32, 35 (2003); 32, 11 (2003); "Organofluorine Compounds," ed. by T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa and M. Shimizu, Springer-Verlag, Berlin, Heidelberg (2000); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by V. A. Soloshonok, Wiley, Chichester (1999); "Organofluorine Chemistry," ed. by R. D. Chambers, Springer, Berlin (1997); K. Iseki, Tetrahedron, 54, 13887 (1998); "Biomedical Frontiers of Fluorine Chemistry," ed. by I. Ojima, J. R. McCarthy, and J. T. Welch, American Chemical Society, Washington DC (1996); Thematic issue of fluorine chemistry, "Chem. Rev.," ed. by B. E. Smart (1996), Vol. 96; "Organofluorine Chemistry: Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum Press, New York (1994); "Chemistry of Fluorine," T. Kitazume, T. Ishihara, and T. Taguchi, Koudansha, Tokyo (1993); "Synthesis and Reactivity of Fluorocompounds," ed. by N. Ishikawa, CMC, Tokyo (1987), Vol. 3; N. Ishikawa and Y. Kobayashi, "Fluorine Compounds," Koudansha, Tokyo (1979); "Chemistry of Organic Fluorine Compounds," 2nd ed., ed. by M. Hudlicky, Ellis Horwood, Chichester (1976).
2. K. Mikami, Y. Itoh, and M. Yamanaka, Chem. Rev., 104, 1 (2004); Fine Chemical 32, 35 (2003); 32, 11 (2003); "Organofluorine Compounds," ed. by T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa and M. Shimizu, Springer-Verlag, Berlin, Heidelberg (2000); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by V. A. Soloshonok, Wiley, Chichester (1999); "Organofluorine Chemistry," ed. by R. D. Chambers, Springer, Berlin (1997); K. Iseki, Tetrahedron, 54, 13887 (1998); "Biomedical Frontiers of Fluorine Chemistry," ed. by I. Ojima, J. R. McCarthy, and J. T. Welch, American Chemical Society, Washington DC (1996); Thematic issue of fluorine chemistry, "Chem. Rev.," ed. by B. E. Smart (1996), Vol. 96; "Organofluorine Chemistry: Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum Press, New York (1994); "Chemistry of Fluorine," T. Kitazume, T. Ishihara, and T. Taguchi, Koudansha, Tokyo (1993); "Synthesis and Reactivity of Fluorocompounds," ed. by N. Ishikawa, CMC, Tokyo (1987), Vol. 3; N. Ishikawa and Y. Kobayashi, "Fluorine Compounds," Koudansha, Tokyo (1979); "Chemistry of Organic Fluorine Compounds," 2nd ed., ed. by M. Hudlicky, Ellis Horwood, Chichester (1976).
3. K. Mikami, Y. Itoh, and M. Yamanaka, Chem. Rev., 104, 1 (2004); Fine Chemical 32, 35 (2003); 32, 11 (2003); "Organofluorine Compounds," ed. by T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa and M. Shimizu, Springer-Verlag, Berlin, Heidelberg (2000); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by V. A. Soloshonok, Wiley, Chichester (1999); "Organofluorine Chemistry," ed. by R. D. Chambers, Springer, Berlin (1997); K. Iseki, Tetrahedron, 54, 13887 (1998); "Biomedical Frontiers of Fluorine Chemistry," ed. by I. Ojima, J. R. McCarthy, and J. T. Welch, American Chemical Society, Washington DC (1996); Thematic issue of fluorine chemistry, "Chem. Rev.," ed. by B. E. Smart (1996), Vol. 96; "Organofluorine Chemistry: Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum Press, New York (1994); "Chemistry of Fluorine," T. Kitazume, T. Ishihara, and T. Taguchi, Koudansha, Tokyo (1993); "Synthesis and Reactivity of Fluorocompounds," ed. by N. Ishikawa, CMC, Tokyo (1987), Vol. 3; N. Ishikawa and Y. Kobayashi, "Fluorine Compounds," Koudansha, Tokyo (1979); "Chemistry of Organic Fluorine Compounds," 2nd ed., ed. by M. Hudlicky, Ellis Horwood, Chichester (1976).
4. K. Mikami, Y. Itoh, and M. Yamanaka, Chem. Rev., 104, 1 (2004); Fine Chemical 32, 35 (2003); 32, 11 (2003); "Organofluorine Compounds," ed. by T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa and M. Shimizu, Springer-Verlag, Berlin, Heidelberg (2000); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by V. A. Soloshonok, Wiley, Chichester (1999); "Organofluorine Chemistry," ed. by R. D. Chambers, Springer, Berlin (1997); K. Iseki, Tetrahedron, 54, 13887 (1998); "Biomedical Frontiers of Fluorine Chemistry," ed. by I. Ojima, J. R. McCarthy, and J. T. Welch, American Chemical Society, Washington DC (1996); Thematic issue of fluorine chemistry, "Chem. Rev.," ed. by B. E. Smart (1996), Vol. 96; "Organofluorine Chemistry: Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum Press, New York (1994); "Chemistry of Fluorine," T. Kitazume, T. Ishihara, and T. Taguchi, Koudansha, Tokyo (1993); "Synthesis and Reactivity of Fluorocompounds," ed. by N. Ishikawa, CMC, Tokyo (1987), Vol. 3; N. Ishikawa and Y. Kobayashi, "Fluorine Compounds," Koudansha, Tokyo (1979); "Chemistry of Organic Fluorine Compounds," 2nd ed., ed. by M. Hudlicky, Ellis Horwood, Chichester (1976).
5. K. Mikami, Y. Itoh, and M. Yamanaka, Chem. Rev., 104, 1 (2004); Fine Chemical 32, 35 (2003); 32, 11 (2003); "Organofluorine Compounds," ed. by T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa and M. Shimizu, Springer-Verlag, Berlin, Heidelberg (2000); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by V. A. Soloshonok, Wiley, Chichester (1999); "Organofluorine Chemistry," ed. by R. D. Chambers, Springer, Berlin (1997); K. Iseki, Tetrahedron, 54, 13887 (1998); "Biomedical Frontiers of Fluorine Chemistry," ed. by I. Ojima, J. R. McCarthy, and J. T. Welch, American Chemical Society, Washington DC (1996); Thematic issue of fluorine chemistry, "Chem. Rev.," ed. by B. E. Smart (1996), Vol. 96; "Organofluorine Chemistry: Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum Press, New York (1994); "Chemistry of Fluorine," T. Kitazume, T. Ishihara, and T. Taguchi, Koudansha, Tokyo (1993); "Synthesis and Reactivity of Fluorocompounds," ed. by N. Ishikawa, CMC, Tokyo (1987), Vol. 3; N. Ishikawa and Y. Kobayashi, "Fluorine Compounds," Koudansha, Tokyo (1979); "Chemistry of Organic Fluorine Compounds," 2nd ed., ed. by M. Hudlicky, Ellis Horwood, Chichester (1976).
6. K. Mikami, Y. Itoh, and M. Yamanaka, Chem. Rev., 104, 1 (2004); Fine Chemical 32, 35 (2003); 32, 11 (2003); "Organofluorine Compounds," ed. by T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa and M. Shimizu, Springer-Verlag, Berlin, Heidelberg (2000); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by V. A. Soloshonok, Wiley, Chichester (1999); "Organofluorine Chemistry," ed. by R. D. Chambers, Springer, Berlin (1997); K. Iseki, Tetrahedron, 54, 13887 (1998); "Biomedical Frontiers of Fluorine Chemistry," ed. by I. Ojima, J. R. McCarthy, and J. T. Welch, American Chemical Society, Washington DC (1996); Thematic issue of fluorine chemistry, "Chem. Rev.," ed. by B. E. Smart (1996), Vol. 96; "Organofluorine Chemistry: Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum Press, New York (1994); "Chemistry of Fluorine," T. Kitazume, T. Ishihara, and T. Taguchi, Koudansha, Tokyo (1993); "Synthesis and Reactivity of Fluorocompounds," ed. by N. Ishikawa, CMC, Tokyo (1987), Vol. 3; N. Ishikawa and Y. Kobayashi, "Fluorine Compounds," Koudansha, Tokyo (1979); "Chemistry of Organic Fluorine Compounds," 2nd ed., ed. by M. Hudlicky, Ellis Horwood, Chichester (1976).
7. K. Mikami, Y. Itoh, and M. Yamanaka, Chem. Rev., 104, 1 (2004); Fine Chemical 32, 35 (2003); 32, 11 (2003); "Organofluorine Compounds," ed. by T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa and M. Shimizu, Springer-Verlag, Berlin, Heidelberg (2000); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by V. A. Soloshonok, Wiley, Chichester (1999); "Organofluorine Chemistry," ed. by R. D. Chambers, Springer, Berlin (1997); K. Iseki, Tetrahedron, 54, 13887 (1998); "Biomedical Frontiers of Fluorine Chemistry," ed. by I. Ojima, J. R. McCarthy, and J. T. Welch, American Chemical Society, Washington DC (1996); Thematic issue of fluorine chemistry, "Chem. Rev.," ed. by B. E. Smart (1996), Vol. 96; "Organofluorine Chemistry: Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum Press, New York (1994); "Chemistry of Fluorine," T. Kitazume, T. Ishihara, and T. Taguchi, Koudansha, Tokyo (1993); "Synthesis and Reactivity of Fluorocompounds," ed. by N. Ishikawa, CMC, Tokyo (1987), Vol. 3; N. Ishikawa and Y. Kobayashi, "Fluorine Compounds," Koudansha, Tokyo (1979); "Chemistry of Organic Fluorine Compounds," 2nd ed., ed. by M. Hudlicky, Ellis Horwood, Chichester (1976).
8. K. Mikami, Y. Itoh, and M. Yamanaka, Chem. Rev., 104, 1 (2004); Fine Chemical 32, 35 (2003); 32, 11 (2003); "Organofluorine Compounds," ed. by T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa and M. Shimizu, Springer-Verlag, Berlin, Heidelberg (2000); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by V. A. Soloshonok, Wiley, Chichester (1999); "Organofluorine Chemistry," ed. by R. D. Chambers, Springer, Berlin (1997); K. Iseki, Tetrahedron, 54, 13887 (1998); "Biomedical Frontiers of Fluorine Chemistry," ed. by I. Ojima, J. R. McCarthy, and J. T. Welch, American Chemical Society, Washington DC (1996); Thematic issue of fluorine chemistry, "Chem. Rev.," ed. by B. E. Smart (1996), Vol. 96; "Organofluorine Chemistry: Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum Press, New York (1994); "Chemistry of Fluorine," T. Kitazume, T. Ishihara, and T. Taguchi, Koudansha, Tokyo (1993); "Synthesis and Reactivity of Fluorocompounds," ed. by N. Ishikawa, CMC, Tokyo (1987), Vol. 3; N. Ishikawa and Y. Kobayashi, "Fluorine Compounds," Koudansha, Tokyo (1979); "Chemistry of Organic Fluorine Compounds," 2nd ed., ed. by M. Hudlicky, Ellis Horwood, Chichester (1976).
9. K. Mikami, Y. Itoh, and M. Yamanaka, Chem. Rev., 104, 1 (2004); Fine Chemical 32, 35 (2003); 32, 11 (2003); "Organofluorine Compounds," ed. by T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa and M. Shimizu, Springer-Verlag, Berlin, Heidelberg (2000); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by V. A. Soloshonok, Wiley, Chichester (1999); "Organofluorine Chemistry," ed. by R. D. Chambers, Springer, Berlin (1997); K. Iseki, Tetrahedron, 54, 13887 (1998); "Biomedical Frontiers of Fluorine Chemistry," ed. by I. Ojima, J. R. McCarthy, and J. T. Welch, American Chemical Society, Washington DC (1996); Thematic issue of fluorine chemistry, "Chem. Rev.," ed. by B. E. Smart (1996), Vol. 96; "Organofluorine Chemistry: Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum Press, New York (1994); "Chemistry of Fluorine," T. Kitazume, T. Ishihara, and T. Taguchi, Koudansha, Tokyo (1993); "Synthesis and Reactivity of Fluorocompounds," ed. by N. Ishikawa, CMC, Tokyo (1987), Vol. 3; N. Ishikawa and Y. Kobayashi, "Fluorine Compounds," Koudansha, Tokyo (1979); "Chemistry of Organic Fluorine Compounds," 2nd ed., ed. by M. Hudlicky, Ellis Horwood, Chichester (1976).
10. K. Mikami, Y. Itoh, and M. Yamanaka, Chem. Rev., 104, 1 (2004); Fine Chemical 32, 35 (2003); 32, 11 (2003); "Organofluorine Compounds," ed. by T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa and M. Shimizu, Springer-Verlag, Berlin, Heidelberg (2000); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by V. A. Soloshonok, Wiley, Chichester (1999); "Organofluorine Chemistry," ed. by R. D. Chambers, Springer, Berlin (1997); K. Iseki, Tetrahedron, 54, 13887 (1998); "Biomedical Frontiers of Fluorine Chemistry," ed. by I. Ojima, J. R. McCarthy, and J. T. Welch, American Chemical Society, Washington DC (1996); Thematic issue of fluorine chemistry, "Chem. Rev.," ed. by B. E. Smart (1996), Vol. 96; "Organofluorine Chemistry: Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum Press, New York (1994); "Chemistry of Fluorine," T. Kitazume, T. Ishihara, and T. Taguchi, Koudansha, Tokyo (1993); "Synthesis and Reactivity of Fluorocompounds," ed. by N. Ishikawa, CMC, Tokyo (1987), Vol. 3; N. Ishikawa and Y. Kobayashi, "Fluorine Compounds," Koudansha, Tokyo (1979); "Chemistry of Organic Fluorine Compounds," 2nd ed., ed. by M. Hudlicky, Ellis Horwood, Chichester (1976).
11. K. Mikami, Y. Itoh, and M. Yamanaka, Chem. Rev., 104, 1 (2004); Fine Chemical 32, 35 (2003); 32, 11 (2003); "Organofluorine Compounds," ed. by T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa and M. Shimizu, Springer-Verlag, Berlin, Heidelberg (2000); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by V. A. Soloshonok, Wiley, Chichester (1999); "Organofluorine Chemistry," ed. by R. D. Chambers, Springer, Berlin (1997); K. Iseki, Tetrahedron, 54, 13887 (1998); "Biomedical Frontiers of Fluorine Chemistry," ed. by I. Ojima, J. R. McCarthy, and J. T. Welch, American Chemical Society, Washington DC (1996); Thematic issue of fluorine chemistry, "Chem. Rev.," ed. by B. E. Smart (1996), Vol. 96; "Organofluorine Chemistry: Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum Press, New York (1994); "Chemistry of Fluorine," T. Kitazume, T. Ishihara, and T. Taguchi, Koudansha, Tokyo (1993); "Synthesis and Reactivity of Fluorocompounds," ed. by N. Ishikawa, CMC, Tokyo (1987), Vol. 3; N. Ishikawa and Y. Kobayashi, "Fluorine Compounds," Koudansha, Tokyo (1979); "Chemistry of Organic Fluorine Compounds," 2nd ed., ed. by M. Hudlicky, Ellis Horwood, Chichester (1976).
12. K. Mikami, Y. Itoh, and M. Yamanaka, Chem. Rev., 104, 1 (2004); Fine Chemical 32, 35 (2003); 32, 11 (2003); "Organofluorine Compounds," ed. by T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa and M. Shimizu, Springer-Verlag, Berlin, Heidelberg (2000); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by V. A. Soloshonok, Wiley, Chichester (1999); "Organofluorine Chemistry," ed. by R. D. Chambers, Springer, Berlin (1997); K. Iseki, Tetrahedron, 54, 13887 (1998); "Biomedical Frontiers of Fluorine Chemistry," ed. by I. Ojima, J. R. McCarthy, and J. T. Welch, American Chemical Society, Washington DC (1996); Thematic issue of fluorine chemistry, "Chem. Rev.," ed. by B. E. Smart (1996), Vol. 96; "Organofluorine Chemistry: Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum Press, New York (1994); "Chemistry of Fluorine," T. Kitazume, T. Ishihara, and T. Taguchi, Koudansha, Tokyo (1993); "Synthesis and Reactivity of Fluorocompounds," ed. by N. Ishikawa, CMC, Tokyo (1987), Vol. 3; N. Ishikawa and Y. Kobayashi, "Fluorine Compounds," Koudansha, Tokyo (1979); "Chemistry of Organic Fluorine Compounds," 2nd ed., ed. by M. Hudlicky, Ellis Horwood, Chichester (1976).
13. K. Mikami, Y. Itoh, and M. Yamanaka, Chem. Rev., 104, 1 (2004); Fine Chemical 32, 35 (2003); 32, 11 (2003); "Organofluorine Compounds," ed. by T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa and M. Shimizu, Springer-Verlag, Berlin, Heidelberg (2000); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by V. A. Soloshonok, Wiley, Chichester (1999); "Organofluorine Chemistry," ed. by R. D. Chambers, Springer, Berlin (1997); K. Iseki, Tetrahedron, 54, 13887 (1998); "Biomedical Frontiers of Fluorine Chemistry," ed. by I. Ojima, J. R. McCarthy, and J. T. Welch, American Chemical Society, Washington DC (1996); Thematic issue of fluorine chemistry, "Chem. Rev.," ed. by B. E. Smart (1996), Vol. 96; "Organofluorine Chemistry: Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum Press, New York (1994); "Chemistry of Fluorine," T. Kitazume, T. Ishihara, and T. Taguchi, Koudansha, Tokyo (1993); "Synthesis and Reactivity of Fluorocompounds," ed. by N. Ishikawa, CMC, Tokyo (1987), Vol. 3; N. Ishikawa and Y. Kobayashi, "Fluorine Compounds," Koudansha, Tokyo (1979); "Chemistry of Organic Fluorine Compounds," 2nd ed., ed. by M. Hudlicky, Ellis Horwood, Chichester (1976).
14. K. Mikami, Y. Itoh, and M. Yamanaka, Chem. Rev., 104, 1 (2004); Fine Chemical 32, 35 (2003); 32, 11 (2003); "Organofluorine Compounds," ed. by T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa and M. Shimizu, Springer-Verlag, Berlin, Heidelberg (2000); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by V. A. Soloshonok, Wiley, Chichester (1999); "Organofluorine Chemistry," ed. by R. D. Chambers, Springer, Berlin (1997); K. Iseki, Tetrahedron, 54, 13887 (1998); "Biomedical Frontiers of Fluorine Chemistry," ed. by I. Ojima, J. R. McCarthy, and J. T. Welch, American Chemical Society, Washington DC (1996); Thematic issue of fluorine chemistry, "Chem. Rev.," ed. by B. E. Smart (1996), Vol. 96; "Organofluorine Chemistry: Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum Press, New York (1994); "Chemistry of Fluorine," T. Kitazume, T. Ishihara, and T. Taguchi, Koudansha, Tokyo (1993); "Synthesis and Reactivity of Fluorocompounds," ed. by N. Ishikawa, CMC, Tokyo (1987), Vol. 3; N. Ishikawa and Y. Kobayashi, "Fluorine Compounds," Koudansha, Tokyo (1979); "Chemistry of Organic Fluorine Compounds," 2nd ed., ed. by M. Hudlicky, Ellis Horwood, Chichester (1976).
15. T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 102, 5974 (1980).
16. S. Hara, T. Hoshio, M. Kameoka, M. Sawaguchi, T. Fukuhara, and N. Yoneda, Tetrahedron, 55, 4947 (1999); R. Skupin and G. Haufe, J. Fluorine Chem., 92, 157 (1998); A. Sattler and G. Haufe, J. Fluorine Chem., 69, 185 (1994); J. Umezawa, O. Takahashi, K. Furuhashi, and H. Nohira, Tetrahedron: Asymmetry, 4, 2053 (1993); M. W. Hager and D. C. Liotta, Tetrahedron Lett., 33, 7083 (1992); A. A. Nikitenko, B. M. Arshava, I. E. Mikerin, Y. E. Raifeld, V. J. Lee, and S. A. Lang, Jr., Tetrahedron Lett., 33, 7087 (1992); D. Landini and M. Penso, Tetrahedron Lett., 31, 7209 (1990); M. Muehlbacher and C. D. Poulter, J. Org. Chem., 53, 1026 (1988); G. A. Olah and D. Meidar, Isr. J. Chem., 17, 148 (1978).
17. S. Hara, T. Hoshio, M. Kameoka, M. Sawaguchi, T. Fukuhara, and N. Yoneda, Tetrahedron, 55, 4947 (1999); R. Skupin and G. Haufe, J. Fluorine Chem., 92, 157 (1998); A. Sattler and G. Haufe, J. Fluorine Chem., 69, 185 (1994); J. Umezawa, O. Takahashi, K. Furuhashi, and H. Nohira, Tetrahedron: Asymmetry, 4, 2053 (1993); M. W. Hager and D. C. Liotta, Tetrahedron Lett., 33, 7083 (1992); A. A. Nikitenko, B. M. Arshava, I. E. Mikerin, Y. E. Raifeld, V. J. Lee, and S. A. Lang, Jr., Tetrahedron Lett., 33, 7087 (1992); D. Landini and M. Penso, Tetrahedron Lett., 31, 7209 (1990); M. Muehlbacher and C. D. Poulter, J. Org. Chem., 53, 1026 (1988); G. A. Olah and D. Meidar, Isr. J. Chem., 17, 148 (1978).
18. S. Hara, T. Hoshio, M. Kameoka, M. Sawaguchi, T. Fukuhara, and N. Yoneda, Tetrahedron, 55, 4947 (1999); R. Skupin and G. Haufe, J. Fluorine Chem., 92, 157 (1998); A. Sattler and G. Haufe, J. Fluorine Chem., 69, 185 (1994); J. Umezawa, O. Takahashi, K. Furuhashi, and H. Nohira, Tetrahedron: Asymmetry, 4, 2053 (1993); M. W. Hager and D. C. Liotta, Tetrahedron Lett., 33, 7083 (1992); A. A. Nikitenko, B. M. Arshava, I. E. Mikerin, Y. E. Raifeld, V. J. Lee, and S. A. Lang, Jr., Tetrahedron Lett., 33, 7087 (1992); D. Landini and M. Penso, Tetrahedron Lett., 31, 7209 (1990); M. Muehlbacher and C. D. Poulter, J. Org. Chem., 53, 1026 (1988); G. A. Olah and D. Meidar, Isr. J. Chem., 17, 148 (1978).
19. S. Hara, T. Hoshio, M. Kameoka, M. Sawaguchi, T. Fukuhara, and N. Yoneda, Tetrahedron, 55, 4947 (1999); R. Skupin and G. Haufe, J. Fluorine Chem., 92, 157 (1998); A. Sattler and G. Haufe, J. Fluorine Chem., 69, 185 (1994); J. Umezawa, O. Takahashi, K. Furuhashi, and H. Nohira, Tetrahedron: Asymmetry, 4, 2053 (1993); M. W. Hager and D. C. Liotta, Tetrahedron Lett., 33, 7083 (1992); A. A. Nikitenko, B. M. Arshava, I. E. Mikerin, Y. E. Raifeld, V. J. Lee, and S. A. Lang, Jr., Tetrahedron Lett., 33, 7087 (1992); D. Landini and M. Penso, Tetrahedron Lett., 31, 7209 (1990); M. Muehlbacher and C. D. Poulter, J. Org. Chem., 53, 1026 (1988); G. A. Olah and D. Meidar, Isr. J. Chem., 17, 148 (1978).
20. S. Hara, T. Hoshio, M. Kameoka, M. Sawaguchi, T. Fukuhara, and N. Yoneda, Tetrahedron, 55, 4947 (1999); R. Skupin and G. Haufe, J. Fluorine Chem., 92, 157 (1998); A. Sattler and G. Haufe, J. Fluorine Chem., 69, 185 (1994); J. Umezawa, O. Takahashi, K. Furuhashi, and H. Nohira, Tetrahedron: Asymmetry, 4, 2053 (1993); M. W. Hager and D. C. Liotta, Tetrahedron Lett., 33, 7083 (1992); A. A. Nikitenko, B. M. Arshava, I. E. Mikerin, Y. E. Raifeld, V. J. Lee, and S. A. Lang, Jr., Tetrahedron Lett., 33, 7087 (1992); D. Landini and M. Penso, Tetrahedron Lett., 31, 7209 (1990); M. Muehlbacher and C. D. Poulter, J. Org. Chem., 53, 1026 (1988); G. A. Olah and D. Meidar, Isr. J. Chem., 17, 148 (1978).
21. S. Hara, T. Hoshio, M. Kameoka, M. Sawaguchi, T. Fukuhara, and N. Yoneda, Tetrahedron, 55, 4947 (1999); R. Skupin and G. Haufe, J. Fluorine Chem., 92, 157 (1998); A. Sattler and G. Haufe, J. Fluorine Chem., 69, 185 (1994); J. Umezawa, O. Takahashi, K. Furuhashi, and H. Nohira, Tetrahedron: Asymmetry, 4, 2053 (1993); M. W. Hager and D. C. Liotta, Tetrahedron Lett., 33, 7083 (1992); A. A. Nikitenko, B. M. Arshava, I. E. Mikerin, Y. E. Raifeld, V. J. Lee, and S. A. Lang, Jr., Tetrahedron Lett., 33, 7087 (1992); D. Landini and M. Penso, Tetrahedron Lett., 31, 7209 (1990); M. Muehlbacher and C. D. Poulter, J. Org. Chem., 53, 1026 (1988); G. A. Olah and D. Meidar, Isr. J. Chem., 17, 148 (1978).
22. S. Hara, T. Hoshio, M. Kameoka, M. Sawaguchi, T. Fukuhara, and N. Yoneda, Tetrahedron, 55, 4947 (1999); R. Skupin and G. Haufe, J. Fluorine Chem., 92, 157 (1998); A. Sattler and G. Haufe, J. Fluorine Chem., 69, 185 (1994); J. Umezawa, O. Takahashi, K. Furuhashi, and H. Nohira, Tetrahedron: Asymmetry, 4, 2053 (1993); M. W. Hager and D. C. Liotta, Tetrahedron Lett., 33, 7083 (1992); A. A. Nikitenko, B. M. Arshava, I. E. Mikerin, Y. E. Raifeld, V. J. Lee, and S. A. Lang, Jr., Tetrahedron Lett., 33, 7087 (1992); D. Landini and M. Penso, Tetrahedron Lett., 31, 7209 (1990); M. Muehlbacher and C. D. Poulter, J. Org. Chem., 53, 1026 (1988); G. A. Olah and D. Meidar, Isr. J. Chem., 17, 148 (1978).
23. S. Hara, T. Hoshio, M. Kameoka, M. Sawaguchi, T. Fukuhara, and N. Yoneda, Tetrahedron, 55, 4947 (1999); R. Skupin and G. Haufe, J. Fluorine Chem., 92, 157 (1998); A. Sattler and G. Haufe, J. Fluorine Chem., 69, 185 (1994); J. Umezawa, O. Takahashi, K. Furuhashi, and H. Nohira, Tetrahedron: Asymmetry, 4, 2053 (1993); M. W. Hager and D. C. Liotta, Tetrahedron Lett., 33, 7083 (1992); A. A. Nikitenko, B. M. Arshava, I. E. Mikerin, Y. E. Raifeld, V. J. Lee, and S. A. Lang, Jr., Tetrahedron Lett., 33, 7087 (1992); D. Landini and M. Penso, Tetrahedron Lett., 31, 7209 (1990); M. Muehlbacher and C. D. Poulter, J. Org. Chem., 53, 1026 (1988); G. A. Olah and D. Meidar, Isr. J. Chem., 17, 148 (1978).
24. S. Hara, T. Hoshio, M. Kameoka, M. Sawaguchi, T. Fukuhara, and N. Yoneda, Tetrahedron, 55, 4947 (1999); R. Skupin and G. Haufe, J. Fluorine Chem., 92, 157 (1998); A. Sattler and G. Haufe, J. Fluorine Chem., 69, 185 (1994); J. Umezawa, O. Takahashi, K. Furuhashi, and H. Nohira, Tetrahedron: Asymmetry, 4, 2053 (1993); M. W. Hager and D. C. Liotta, Tetrahedron Lett., 33, 7083 (1992); A. A. Nikitenko, B. M. Arshava, I. E. Mikerin, Y. E. Raifeld, V. J. Lee, and S. A. Lang, Jr., Tetrahedron Lett., 33, 7087 (1992); D. Landini and M. Penso, Tetrahedron Lett., 31, 7209 (1990); M. Muehlbacher and C. D. Poulter, J. Org. Chem., 53, 1026 (1988); G. A. Olah and D. Meidar, Isr. J. Chem., 17, 148 (1978).
25. K. Mikami, S. Ohba, and H. Ohmura, J. Organomet. Chem., 662, 77 (2002). Stereo chemical notation is herein revised.
26. 6 was added for D-lock.
27. M. L. Afanasiev, A. D. Vasiliev, V. V. Lisin, A. M. Nazarov, and A. A. Sukhovski, J. Struct. Chem., 38, 556 (1998); A. K. Sengupta and H. S. Dasgupta, Indian J. Chem., 1978, 608; R. S. Borden and R. N. Hammer, Inorg. Chem., 9, 2004 (1970); P. A. W. Dean and D. F. Evans, J. Chem. Soc., 1967, 698; D. S. Dyer and R. O. Ragsdale, J. Phys. Chem., 71, 2309 (1967); D. S. Dyer and R. O. Ragsdale, Inorg. Chem., 6, 8 (1967); D. S. Dyer and R. O. Ragsdale, J. Am. Chem. Soc., 89, 1528 (1967).
28. M. L. Afanasiev, A. D. Vasiliev, V. V. Lisin, A. M. Nazarov, and A. A. Sukhovski, J. Struct. Chem., 38, 556 (1998); A. K. Sengupta and H. S. Dasgupta, Indian J. Chem., 1978, 608; R. S. Borden and R. N. Hammer, Inorg. Chem., 9, 2004 (1970); P. A. W. Dean and D. F. Evans, J. Chem. Soc., 1967, 698; D. S. Dyer and R. O. Ragsdale, J. Phys. Chem., 71, 2309 (1967); D. S. Dyer and R. O. Ragsdale, Inorg. Chem., 6, 8 (1967); D. S. Dyer and R. O. Ragsdale, J. Am. Chem. Soc., 89, 1528 (1967).
29. M. L. Afanasiev, A. D. Vasiliev, V. V. Lisin, A. M. Nazarov, and A. A. Sukhovski, J. Struct. Chem., 38, 556 (1998); A. K. Sengupta and H. S. Dasgupta, Indian J. Chem., 1978, 608; R. S. Borden and R. N. Hammer, Inorg. Chem., 9, 2004 (1970); P. A. W. Dean and D. F. Evans, J. Chem. Soc., 1967, 698; D. S. Dyer and R. O. Ragsdale, J. Phys. Chem., 71, 2309 (1967); D. S. Dyer and R. O. Ragsdale, Inorg. Chem., 6, 8 (1967); D. S. Dyer and R. O. Ragsdale, J. Am. Chem. Soc., 89, 1528 (1967).
30. M. L. Afanasiev, A. D. Vasiliev, V. V. Lisin, A. M. Nazarov, and A. A. Sukhovski, J. Struct. Chem., 38, 556 (1998); A. K. Sengupta and H. S. Dasgupta, Indian J. Chem., 1978, 608; R. S. Borden and R. N. Hammer, Inorg. Chem., 9, 2004 (1970); P. A. W. Dean and D. F. Evans, J. Chem. Soc., 1967, 698; D. S. Dyer and R. O. Ragsdale, J. Phys. Chem., 71, 2309 (1967); D. S. Dyer and R. O. Ragsdale, Inorg. Chem., 6, 8 (1967); D. S. Dyer and R. O. Ragsdale, J. Am. Chem. Soc., 89, 1528 (1967).
31. M. L. Afanasiev, A. D. Vasiliev, V. V. Lisin, A. M. Nazarov, and A. A. Sukhovski, J. Struct. Chem., 38, 556 (1998); A. K. Sengupta and H. S. Dasgupta, Indian J. Chem., 1978, 608; R. S. Borden and R. N. Hammer, Inorg. Chem., 9, 2004 (1970); P. A. W. Dean and D. F. Evans, J. Chem. Soc., 1967, 698; D. S. Dyer and R. O. Ragsdale, J. Phys. Chem., 71, 2309 (1967); D. S. Dyer and R. O. Ragsdale, Inorg. Chem., 6, 8 (1967); D. S. Dyer and R. O. Ragsdale, J. Am. Chem. Soc., 89, 1528 (1967).
32. M. L. Afanasiev, A. D. Vasiliev, V. V. Lisin, A. M. Nazarov, and A. A. Sukhovski, J. Struct. Chem., 38, 556 (1998); A. K. Sengupta and H. S. Dasgupta, Indian J. Chem., 1978, 608; R. S. Borden and R. N. Hammer, Inorg. Chem., 9, 2004 (1970); P. A. W. Dean and D. F. Evans, J. Chem. Soc., 1967, 698; D. S. Dyer and R. O. Ragsdale, J. Phys. Chem., 71, 2309 (1967); D. S. Dyer and R. O. Ragsdale, Inorg. Chem., 6, 8 (1967); D. S. Dyer and R. O. Ragsdale, J. Am. Chem. Soc., 89, 1528 (1967).
33. M. L. Afanasiev, A. D. Vasiliev, V. V. Lisin, A. M. Nazarov, and A. A. Sukhovski, J. Struct. Chem., 38, 556 (1998); A. K. Sengupta and H. S. Dasgupta, Indian J. Chem., 1978, 608; R. S. Borden and R. N. Hammer, Inorg. Chem., 9, 2004 (1970); P. A. W. Dean and D. F. Evans, J. Chem. Soc., 1967, 698; D. S. Dyer and R. O. Ragsdale, J. Phys. Chem., 71, 2309 (1967); D. S. Dyer and R. O. Ragsdale, Inorg. Chem., 6, 8 (1967); D. S. Dyer and R. O. Ragsdale, J. Am. Chem. Soc., 89, 1528 (1967).
34. Y. A. Buslaev, D. S. Dyer, and R. O. Ragsdale, Inorg. Chem., 6, 2208 (1967).
35. K. Mikami, S. Ohba, H. Ohmura, N. Kubodera, K. Nakagawa, and T. Okano, Chirality, 13, 366 (2001).