Highly regioselective allylation of imines with allylic barium reagents

Chemical Communications

Volumn , Issue 3, 1996, Pages 367-368

  Yanagisawa, Akira ^a   Ogasawara, Kazuyoshi ^a   Yasue, Katsutaka ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001089557     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960000367     Document Type: Article

References (24)

1. Reviews: G. Courtois and L. Miginiac, J. Organomet. Chem., 1974, 69, 1; Y. Yamamoto, Acc. Chem. Res., 1987, 20, 243; E. F. Kleinman and R. A. Volkmann, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and C. H. Heathcock, Pergamon, Oxford, 1991, vol. 2, p. 957; Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207.
2. Reviews: G. Courtois and L. Miginiac, J. Organomet. Chem., 1974, 69, 1; Y. Yamamoto, Acc. Chem. Res., 1987, 20, 243; E. F. Kleinman and R. A. Volkmann, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and C. H. Heathcock, Pergamon, Oxford, 1991, vol. 2, p. 957; Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207.
3. Reviews: G. Courtois and L. Miginiac, J. Organomet. Chem., 1974, 69, 1; Y. Yamamoto, Acc. Chem. Res., 1987, 20, 243; E. F. Kleinman and R. A. Volkmann, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and C. H. Heathcock, Pergamon, Oxford, 1991, vol. 2, p. 957; Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207.
4. Reviews: G. Courtois and L. Miginiac, J. Organomet. Chem., 1974, 69, 1; Y. Yamamoto, Acc. Chem. Res., 1987, 20, 243; E. F. Kleinman and R. A. Volkmann, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and C. H. Heathcock, Pergamon, Oxford, 1991, vol. 2, p. 957; Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207.
5. C. Bouchoule and P. Miginiac, C. R. Hebd. Seances Acad. Sci., Ser. C, 1968, 266, 1614; L. Miginiac and B. Mauzé, Bull. Soc. Chim. Fr., 1968, 3832.
6. C. Bouchoule and P. Miginiac, C. R. Hebd. Seances Acad. Sci., Ser. C, 1968, 266, 1614; L. Miginiac and B. Mauzé, Bull. Soc. Chim. Fr., 1968, 3832.
7. A. Yanagisawa, S. Habaue, K. Yasue and H. Yamamoto, J. Am. Chem. Soc., 1994, 116, 6130.
8. Diastereoselective γ-allylation of aldehydes using stereochemically homogeneous allylic barium reagents: S. Habaue, K. Yasue, A. Yanagisawa and H. Yamamoto, Synlett, 1993, 788.
9. G. E. Keck and E. J. Enholm, J. Org. Chem., 1985, 50, 146; Y. Yamamoto, T. Komatsu and K. Maruyama, J. Org. Chem., 1985, 50, 3115.
10. G. E. Keck and E. J. Enholm, J. Org. Chem., 1985, 50, 146; Y. Yamamoto, T. Komatsu and K. Maruyama, J. Org. Chem., 1985, 50, 3115.
11. For additions of organometal reagents (Li, Ce, Yb) to SAMP-hydrazones, see: D. Enders, H. Schubert and C. Nübling, Angew. Chem., Int. Ed. Engl., 1986, 25, 1109; S. E. Denmark, T. Weber and D. W. Piotrowski, J. Am. Chem. Soc., 1987, 109, 2224; T. Weber, J. P. Edwards and S. E. Denmark, Synlett, 1989, 20; D. Enders and D. Bartzen, Liebigs Ann. Chem., 1991, 569; D. Enders, R. Funk, M. Klatt, G. Raabe and E. R. Hovestreydt, Angew. Chem., Int. Ed. Engl., 1993, 32, 418; D. Enders and J. Tiebes, Liebigs Ann. Chem., 1993, 173; D. Enders, M. Klatt and R. Funk, Synlett, 1993, 226.
12. For additions of organometal reagents (Li, Ce, Yb) to SAMP-hydrazones, see: D. Enders, H. Schubert and C. Nübling, Angew. Chem., Int. Ed. Engl., 1986, 25, 1109; S. E. Denmark, T. Weber and D. W. Piotrowski, J. Am. Chem. Soc., 1987, 109, 2224; T. Weber, J. P. Edwards and S. E. Denmark, Synlett, 1989, 20; D. Enders and D. Bartzen, Liebigs Ann. Chem., 1991, 569; D. Enders, R. Funk, M. Klatt, G. Raabe and E. R. Hovestreydt, Angew. Chem., Int. Ed. Engl., 1993, 32, 418; D. Enders and J. Tiebes, Liebigs Ann. Chem., 1993, 173; D. Enders, M. Klatt and R. Funk, Synlett, 1993, 226.
13. For additions of organometal reagents (Li, Ce, Yb) to SAMP-hydrazones, see: D. Enders, H. Schubert and C. Nübling, Angew. Chem., Int. Ed. Engl., 1986, 25, 1109; S. E. Denmark, T. Weber and D. W. Piotrowski, J. Am. Chem. Soc., 1987, 109, 2224; T. Weber, J. P. Edwards and S. E. Denmark, Synlett, 1989, 20; D. Enders and D. Bartzen, Liebigs Ann. Chem., 1991, 569; D. Enders, R. Funk, M. Klatt, G. Raabe and E. R. Hovestreydt, Angew. Chem., Int. Ed. Engl., 1993, 32, 418; D. Enders and J. Tiebes, Liebigs Ann. Chem., 1993, 173; D. Enders, M. Klatt and R. Funk, Synlett, 1993, 226.
14. For additions of organometal reagents (Li, Ce, Yb) to SAMP-hydrazones, see: D. Enders, H. Schubert and C. Nübling, Angew. Chem., Int. Ed. Engl., 1986, 25, 1109; S. E. Denmark, T. Weber and D. W. Piotrowski, J. Am. Chem. Soc., 1987, 109, 2224; T. Weber, J. P. Edwards and S. E. Denmark, Synlett, 1989, 20; D. Enders and D. Bartzen, Liebigs Ann. Chem., 1991, 569; D. Enders, R. Funk, M. Klatt, G. Raabe and E. R. Hovestreydt, Angew. Chem., Int. Ed. Engl., 1993, 32, 418; D. Enders and J. Tiebes, Liebigs Ann. Chem., 1993, 173; D. Enders, M. Klatt and R. Funk, Synlett, 1993, 226.
15. For additions of organometal reagents (Li, Ce, Yb) to SAMP-hydrazones, see: D. Enders, H. Schubert and C. Nübling, Angew. Chem., Int. Ed. Engl., 1986, 25, 1109; S. E. Denmark, T. Weber and D. W. Piotrowski, J. Am. Chem. Soc., 1987, 109, 2224; T. Weber, J. P. Edwards and S. E. Denmark, Synlett, 1989, 20; D. Enders and D. Bartzen, Liebigs Ann. Chem., 1991, 569; D. Enders, R. Funk, M. Klatt, G. Raabe and E. R. Hovestreydt, Angew. Chem., Int. Ed. Engl., 1993, 32, 418; D. Enders and J. Tiebes, Liebigs Ann. Chem., 1993, 173; D. Enders, M. Klatt and R. Funk, Synlett, 1993, 226.
16. For additions of organometal reagents (Li, Ce, Yb) to SAMP-hydrazones, see: D. Enders, H. Schubert and C. Nübling, Angew. Chem., Int. Ed. Engl., 1986, 25, 1109; S. E. Denmark, T. Weber and D. W. Piotrowski, J. Am. Chem. Soc., 1987, 109, 2224; T. Weber, J. P. Edwards and S. E. Denmark, Synlett, 1989, 20; D. Enders and D. Bartzen, Liebigs Ann. Chem., 1991, 569; D. Enders, R. Funk, M. Klatt, G. Raabe and E. R. Hovestreydt, Angew. Chem., Int. Ed. Engl., 1993, 32, 418; D. Enders and J. Tiebes, Liebigs Ann. Chem., 1993, 173; D. Enders, M. Klatt and R. Funk, Synlett, 1993, 226.
17. For additions of organometal reagents (Li, Ce, Yb) to SAMP-hydrazones, see: D. Enders, H. Schubert and C. Nübling, Angew. Chem., Int. Ed. Engl., 1986, 25, 1109; S. E. Denmark, T. Weber and D. W. Piotrowski, J. Am. Chem. Soc., 1987, 109, 2224; T. Weber, J. P. Edwards and S. E. Denmark, Synlett, 1989, 20; D. Enders and D. Bartzen, Liebigs Ann. Chem., 1991, 569; D. Enders, R. Funk, M. Klatt, G. Raabe and E. R. Hovestreydt, Angew. Chem., Int. Ed. Engl., 1993, 32, 418; D. Enders and J. Tiebes, Liebigs Ann. Chem., 1993, 173; D. Enders, M. Klatt and R. Funk, Synlett, 1993, 226.
18. Reversibility in the reactions of γ-monosubstituted allyllithium, magnesium and zinc reagents with aldimines has been observed at room temperature: L. Miginiac and B. Mauzé, Bull. Soc. Chim. Fr., 1968, 4674; B. Mauzé and L. Miginiac, Bull. Soc. Chim. Fr., 1973, 1832; B. Mauzé and L. Miginiac, Bull. Soc. Chim. Fr., 1973, 1082; B. Mauzé and L. Miginiac, Bull. Soc. Chim. Fr., 1973, 1838.
19. Reversibility in the reactions of γ-monosubstituted allyllithium, magnesium and zinc reagents with aldimines has been observed at room temperature: L. Miginiac and B. Mauzé, Bull. Soc. Chim. Fr., 1968, 4674; B. Mauzé and L. Miginiac, Bull. Soc. Chim. Fr., 1973, 1832; B. Mauzé and L. Miginiac, Bull. Soc. Chim. Fr., 1973, 1082; B. Mauzé and L. Miginiac, Bull. Soc. Chim. Fr., 1973, 1838.
20. Reversibility in the reactions of γ-monosubstituted allyllithium, magnesium and zinc reagents with aldimines has been observed at room temperature: L. Miginiac and B. Mauzé, Bull. Soc. Chim. Fr., 1968, 4674; B. Mauzé and L. Miginiac, Bull. Soc. Chim. Fr., 1973, 1832; B. Mauzé and L. Miginiac, Bull. Soc. Chim. Fr., 1973, 1082; B. Mauzé and L. Miginiac, Bull. Soc. Chim. Fr., 1973, 1838.
21. Reversibility in the reactions of γ-monosubstituted allyllithium, magnesium and zinc reagents with aldimines has been observed at room temperature: L. Miginiac and B. Mauzé, Bull. Soc. Chim. Fr., 1968, 4674; B. Mauzé and L. Miginiac, Bull. Soc. Chim. Fr., 1973, 1832; B. Mauzé and L. Miginiac, Bull. Soc. Chim. Fr., 1973, 1082; B. Mauzé and L. Miginiac, Bull. Soc. Chim. Fr., 1973, 1838.
22. N. L. Holy, Chem. Rev., 1974, 74, 243; T. Cohen and M. Bhupathy, Acc. Chem. Res., 1989, 22, 152.
23. N. L. Holy, Chem. Rev., 1974, 74, 243; T. Cohen and M. Bhupathy, Acc. Chem. Res., 1989, 22, 152.
24. T. P. Burns and R. D. Rieke, J. Org. Chem., 1987, 52, 3674.