Enantioselective Dehydrohalogenation Using Chiral Alkoxides: Design of a Catalytic System Allowing Access to Axially Dissymmetric Compounds

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5541-5546

  Amadji, Morad ^a   Vadecard, Jérôme ^a   Cahard, Dominique ^a   Duhamel, Lucette ^a   Duhamel, Pierre ^a   Plaquevent, Jean Christophe ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001690376     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9806456     Document Type: Article

References (40)

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12. For reviews (stoichiometric conditions), see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Simpkins, N. S. Chem. Ind. 20 June 1988, 387-389. (c) Koga, K. Yuki Goxi Kagaku Kyokaishi 1990, 463-475. (d) Waldmann, H. Nachr. Chem. Technol. Lab. 1991, 39, 413-418. (e) Reed, F. Spec. Chem. 1991, 11, 148-151. (f) Koga, K. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; Chapter 5, pp 67-86. (g) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694. (h) Waldmann, H. In Organic Synthetic Highlights II; 1995; pp 19-27. (i) Koga, K. In New Methods in Drugs Research; 1995; Vol. 4, pp 25-39. (j) Koga, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed., 1994; pp 97-116, For examples of catalytic versions, see: (k) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796. (l) Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn 1995, 53, 1021-1032. (m) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428. (n) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (o) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
13. For reviews (stoichiometric conditions), see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Simpkins, N. S. Chem. Ind. 20 June 1988, 387-389. (c) Koga, K. Yuki Goxi Kagaku Kyokaishi 1990, 463-475. (d) Waldmann, H. Nachr. Chem. Technol. Lab. 1991, 39, 413-418. (e) Reed, F. Spec. Chem. 1991, 11, 148-151. (f) Koga, K. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; Chapter 5, pp 67-86. (g) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694. (h) Waldmann, H. In Organic Synthetic Highlights II; 1995; pp 19-27. (i) Koga, K. In New Methods in Drugs Research; 1995; Vol. 4, pp 25-39. (j) Koga, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed., 1994; pp 97-116, For examples of catalytic versions, see: (k) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796. (l) Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn 1995, 53, 1021-1032. (m) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428. (n) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (o) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
14. For reviews (stoichiometric conditions), see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Simpkins, N. S. Chem. Ind. 20 June 1988, 387-389. (c) Koga, K. Yuki Goxi Kagaku Kyokaishi 1990, 463-475. (d) Waldmann, H. Nachr. Chem. Technol. Lab. 1991, 39, 413-418. (e) Reed, F. Spec. Chem. 1991, 11, 148-151. (f) Koga, K. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; Chapter 5, pp 67-86. (g) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694. (h) Waldmann, H. In Organic Synthetic Highlights II; 1995; pp 19-27. (i) Koga, K. In New Methods in Drugs Research; 1995; Vol. 4, pp 25-39. (j) Koga, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed., 1994; pp 97-116, For examples of catalytic versions, see: (k) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796. (l) Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn 1995, 53, 1021-1032. (m) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428. (n) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (o) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
15. For reviews (stoichiometric conditions), see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Simpkins, N. S. Chem. Ind. 20 June 1988, 387-389. (c) Koga, K. Yuki Goxi Kagaku Kyokaishi 1990, 463-475. (d) Waldmann, H. Nachr. Chem. Technol. Lab. 1991, 39, 413-418. (e) Reed, F. Spec. Chem. 1991, 11, 148-151. (f) Koga, K. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; Chapter 5, pp 67-86. (g) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694. (h) Waldmann, H. In Organic Synthetic Highlights II; 1995; pp 19-27. (i) Koga, K. In New Methods in Drugs Research; 1995; Vol. 4, pp 25-39. (j) Koga, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed., 1994; pp 97-116, For examples of catalytic versions, see: (k) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796. (l) Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn 1995, 53, 1021-1032. (m) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428. (n) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (o) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
16. For reviews (stoichiometric conditions), see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Simpkins, N. S. Chem. Ind. 20 June 1988, 387-389. (c) Koga, K. Yuki Goxi Kagaku Kyokaishi 1990, 463-475. (d) Waldmann, H. Nachr. Chem. Technol. Lab. 1991, 39, 413-418. (e) Reed, F. Spec. Chem. 1991, 11, 148-151. (f) Koga, K. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; Chapter 5, pp 67-86. (g) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694. (h) Waldmann, H. In Organic Synthetic Highlights II; 1995; pp 19-27. (i) Koga, K. In New Methods in Drugs Research; 1995; Vol. 4, pp 25-39. (j) Koga, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed., 1994; pp 97-116, For examples of catalytic versions, see: (k) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796. (l) Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn 1995, 53, 1021-1032. (m) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428. (n) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (o) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
17. For reviews (stoichiometric conditions), see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Simpkins, N. S. Chem. Ind. 20 June 1988, 387-389. (c) Koga, K. Yuki Goxi Kagaku Kyokaishi 1990, 463-475. (d) Waldmann, H. Nachr. Chem. Technol. Lab. 1991, 39, 413-418. (e) Reed, F. Spec. Chem. 1991, 11, 148-151. (f) Koga, K. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; Chapter 5, pp 67-86. (g) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694. (h) Waldmann, H. In Organic Synthetic Highlights II; 1995; pp 19-27. (i) Koga, K. In New Methods in Drugs Research; 1995; Vol. 4, pp 25-39. (j) Koga, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed., 1994; pp 97-116, For examples of catalytic versions, see: (k) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796. (l) Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn 1995, 53, 1021-1032. (m) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428. (n) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (o) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
18. For reviews (stoichiometric conditions), see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Simpkins, N. S. Chem. Ind. 20 June 1988, 387-389. (c) Koga, K. Yuki Goxi Kagaku Kyokaishi 1990, 463-475. (d) Waldmann, H. Nachr. Chem. Technol. Lab. 1991, 39, 413-418. (e) Reed, F. Spec. Chem. 1991, 11, 148-151. (f) Koga, K. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; Chapter 5, pp 67-86. (g) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694. (h) Waldmann, H. In Organic Synthetic Highlights II; 1995; pp 19-27. (i) Koga, K. In New Methods in Drugs Research; 1995; Vol. 4, pp 25-39. (j) Koga, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed., 1994; pp 97-116, For examples of catalytic versions, see: (k) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796. (l) Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn 1995, 53, 1021-1032. (m) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428. (n) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (o) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
19. For reviews (stoichiometric conditions), see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Simpkins, N. S. Chem. Ind. 20 June 1988, 387-389. (c) Koga, K. Yuki Goxi Kagaku Kyokaishi 1990, 463-475. (d) Waldmann, H. Nachr. Chem. Technol. Lab. 1991, 39, 413-418. (e) Reed, F. Spec. Chem. 1991, 11, 148-151. (f) Koga, K. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; Chapter 5, pp 67-86. (g) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694. (h) Waldmann, H. In Organic Synthetic Highlights II; 1995; pp 19-27. (i) Koga, K. In New Methods in Drugs Research; 1995; Vol. 4, pp 25-39. (j) Koga, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed., 1994; pp 97-116, For examples of catalytic versions, see: (k) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796. (l) Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn 1995, 53, 1021-1032. (m) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428. (n) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (o) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
20. For reviews (stoichiometric conditions), see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Simpkins, N. S. Chem. Ind. 20 June 1988, 387-389. (c) Koga, K. Yuki Goxi Kagaku Kyokaishi 1990, 463-475. (d) Waldmann, H. Nachr. Chem. Technol. Lab. 1991, 39, 413-418. (e) Reed, F. Spec. Chem. 1991, 11, 148-151. (f) Koga, K. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; Chapter 5, pp 67-86. (g) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694. (h) Waldmann, H. In Organic Synthetic Highlights II; 1995; pp 19-27. (i) Koga, K. In New Methods in Drugs Research; 1995; Vol. 4, pp 25-39. (j) Koga, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed., 1994; pp 97-116, For examples of catalytic versions, see: (k) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796. (l) Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn 1995, 53, 1021-1032. (m) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428. (n) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (o) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
21. For reviews (stoichiometric conditions), see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Simpkins, N. S. Chem. Ind. 20 June 1988, 387-389. (c) Koga, K. Yuki Goxi Kagaku Kyokaishi 1990, 463-475. (d) Waldmann, H. Nachr. Chem. Technol. Lab. 1991, 39, 413-418. (e) Reed, F. Spec. Chem. 1991, 11, 148-151. (f) Koga, K. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; Chapter 5, pp 67-86. (g) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694. (h) Waldmann, H. In Organic Synthetic Highlights II; 1995; pp 19-27. (i) Koga, K. In New Methods in Drugs Research; 1995; Vol. 4, pp 25-39. (j) Koga, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed., 1994; pp 97-116, For examples of catalytic versions, see: (k) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796. (l) Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn 1995, 53, 1021-1032. (m) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428. (n) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (o) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
22. For reviews (stoichiometric conditions), see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Simpkins, N. S. Chem. Ind. 20 June 1988, 387-389. (c) Koga, K. Yuki Goxi Kagaku Kyokaishi 1990, 463-475. (d) Waldmann, H. Nachr. Chem. Technol. Lab. 1991, 39, 413-418. (e) Reed, F. Spec. Chem. 1991, 11, 148-151. (f) Koga, K. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; Chapter 5, pp 67-86. (g) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694. (h) Waldmann, H. In Organic Synthetic Highlights II; 1995; pp 19-27. (i) Koga, K. In New Methods in Drugs Research; 1995; Vol. 4, pp 25-39. (j) Koga, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed., 1994; pp 97-116, For examples of catalytic versions, see: (k) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796. (l) Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn 1995, 53, 1021-1032. (m) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428. (n) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (o) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
23. For reviews (stoichiometric conditions), see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Simpkins, N. S. Chem. Ind. 20 June 1988, 387-389. (c) Koga, K. Yuki Goxi Kagaku Kyokaishi 1990, 463-475. (d) Waldmann, H. Nachr. Chem. Technol. Lab. 1991, 39, 413-418. (e) Reed, F. Spec. Chem. 1991, 11, 148-151. (f) Koga, K. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; Chapter 5, pp 67-86. (g) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694. (h) Waldmann, H. In Organic Synthetic Highlights II; 1995; pp 19-27. (i) Koga, K. In New Methods in Drugs Research; 1995; Vol. 4, pp 25-39. (j) Koga, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed., 1994; pp 97-116, For examples of catalytic versions, see: (k) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796. (l) Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn 1995, 53, 1021-1032. (m) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428. (n) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (o) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
24. For reviews (stoichiometric conditions), see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Simpkins, N. S. Chem. Ind. 20 June 1988, 387-389. (c) Koga, K. Yuki Goxi Kagaku Kyokaishi 1990, 463-475. (d) Waldmann, H. Nachr. Chem. Technol. Lab. 1991, 39, 413-418. (e) Reed, F. Spec. Chem. 1991, 11, 148-151. (f) Koga, K. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; Chapter 5, pp 67-86. (g) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694. (h) Waldmann, H. In Organic Synthetic Highlights II; 1995; pp 19-27. (i) Koga, K. In New Methods in Drugs Research; 1995; Vol. 4, pp 25-39. (j) Koga, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed., 1994; pp 97-116, For examples of catalytic versions, see: (k) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796. (l) Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn 1995, 53, 1021-1032. (m) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428. (n) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (o) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
25. For reviews (stoichiometric conditions), see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26. (b) Simpkins, N. S. Chem. Ind. 20 June 1988, 387-389. (c) Koga, K. Yuki Goxi Kagaku Kyokaishi 1990, 463-475. (d) Waldmann, H. Nachr. Chem. Technol. Lab. 1991, 39, 413-418. (e) Reed, F. Spec. Chem. 1991, 11, 148-151. (f) Koga, K. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; Chapter 5, pp 67-86. (g) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691-694. (h) Waldmann, H. In Organic Synthetic Highlights II; 1995; pp 19-27. (i) Koga, K. In New Methods in Drugs Research; 1995; Vol. 4, pp 25-39. (j) Koga, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed., 1994; pp 97-116, For examples of catalytic versions, see: (k) Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 793-796. (l) Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn 1995, 53, 1021-1032. (m) Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett. 1997, 38, 6425-6428. (n) Tierney, J. P.; Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 1019-1022. (o) Yamashita, T.; Sato, D.; Kiyoto, T.; Kumar, A.; Koga, K. Tetrahedron Lett. 1996, 37, 8195-8198.
26. (a) Vadecard, J.; Plaquevent, J. C.; Duhamel, L.; Duhamel P., J. Chem. Soc., Chem. Commun. 1993, 116-117.
27. (b) Vadecard, J.; Plaquevent, J. C.; Duhamel, L.; Duhamel, P.; Toupet, L. J. Org. Chem. 1994, 59, 2285-2286.
28. See also: Vinj, R. J.; Speckamp, W. N.; De Jong, B. S.; Hiemstra, H. Angew. Chem., Int. Ed. Eng. 1984, 23, 165-166.
29. Amadji, M.; Vadecard, J.; Plaquevent, J. C.; Duhamel, L.; Duhamel, P. J. Am. Chem. Soc. 1996, 118, 12483-12484.
30. Prochiral dibrominated dioxanes 1 were prepared according to: Amadji, M.; Vadecard, J.; Schimmel, U.; Plé, G.; Plaquevent, J. C. J. Chem. Res. (S) 1995, 362-363.
31. Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem. 1991, 56, 4264-4273.
32. Amadji, M.; Cahard, D.; Moriggi, J. D.; Toupet, L.; Plaquevent, J. C. Tetrahedron: Asymmetry 1998, 1657-1660.
33. 5a some reports have been published on enantioselective deprotonation of meso-epoxides (mixed amide-alkoxide bases), see: (a) Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884-885. (b) Hodgson, D. M.; Whitherington, J.; Moloney, B. A. Tetrahedron: Asymmetry 1994, 5, 337-338. (c) Hodgson, D. M.; Whitherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3377. (d) Hodgson, D. M.; Gibbs, A. M. Tetrahedron: Asymmetry 1996, 7, 407-408. (e) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753-755.
34. 5a some reports have been published on enantioselective deprotonation of meso-epoxides (mixed amide-alkoxide bases), see: (a) Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884-885. (b) Hodgson, D. M.; Whitherington, J.; Moloney, B. A. Tetrahedron: Asymmetry 1994, 5, 337-338. (c) Hodgson, D. M.; Whitherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3377. (d) Hodgson, D. M.; Gibbs, A. M. Tetrahedron: Asymmetry 1996, 7, 407-408. (e) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753-755.
35. 5a some reports have been published on enantioselective deprotonation of meso-epoxides (mixed amide-alkoxide bases), see: (a) Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884-885. (b) Hodgson, D. M.; Whitherington, J.; Moloney, B. A. Tetrahedron: Asymmetry 1994, 5, 337-338. (c) Hodgson, D. M.; Whitherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3377. (d) Hodgson, D. M.; Gibbs, A. M. Tetrahedron: Asymmetry 1996, 7, 407-408. (e) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753-755.
36. 5a some reports have been published on enantioselective deprotonation of meso-epoxides (mixed amide-alkoxide bases), see: (a) Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884-885. (b) Hodgson, D. M.; Whitherington, J.; Moloney, B. A. Tetrahedron: Asymmetry 1994, 5, 337-338. (c) Hodgson, D. M.; Whitherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3377. (d) Hodgson, D. M.; Gibbs, A. M. Tetrahedron: Asymmetry 1996, 7, 407-408. (e) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753-755.
37. 5a some reports have been published on enantioselective deprotonation of meso-epoxides (mixed amide-alkoxide bases), see: (a) Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884-885. (b) Hodgson, D. M.; Whitherington, J.; Moloney, B. A. Tetrahedron: Asymmetry 1994, 5, 337-338. (c) Hodgson, D. M.; Whitherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3377. (d) Hodgson, D. M.; Gibbs, A. M. Tetrahedron: Asymmetry 1996, 7, 407-408. (e) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753-755.
38. For the use of cyclic acetals in synthesis, see, for example: (a) Frauenrath, H. Synthesis 1989, 721-734. (b) Enders, D.; Bockstiegel, B. Synthesis 1989, 493-496. (c) Seebach, D.; Lapierre, J. M.; Jaworek, W.; Seiler, P. Helv. Chim. Acta 1991, 56, 4264-4268.
39. For the use of cyclic acetals in synthesis, see, for example: (a) Frauenrath, H. Synthesis 1989, 721-734. (b) Enders, D.; Bockstiegel, B. Synthesis 1989, 493-496. (c) Seebach, D.; Lapierre, J. M.; Jaworek, W.; Seiler, P. Helv. Chim. Acta 1991, 56, 4264-4268.
40. For the use of cyclic acetals in synthesis, see, for example: (a) Frauenrath, H. Synthesis 1989, 721-734. (b) Enders, D.; Bockstiegel, B. Synthesis 1989, 493-496. (c) Seebach, D.; Lapierre, J. M.; Jaworek, W.; Seiler, P. Helv. Chim. Acta 1991, 56, 4264-4268.