New chiral 3-naphthylaminomethylpyrrolidines: An unexpected epimerisation reaction

Heterocycles

Volumn 51, Issue 10, 1999, Pages 2463-2470

  Fava, Cristiana ^a   Galeazzi, Roberta ^a   Mobbili, Giovanna ^a   Orena, Mario ^a  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; BENZALDEHYDE; PROPANOL; PYRROLIDINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHIRALITY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033214198     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8648     Document Type: Article

References (16)

1. S. Kobayashi and T. Mukaiyama, Chem. Lett., 1989, 297; S. Kobayashi, H. Uchiro, Y. Fujishita, I. Shiina and T. Mukaiyama, J. Am. Chem. Soc., 1991, 113, 4247; S. Kobayashi and M. Horibe, J. Am. Chem. Soc., 1994, 116, 9805; S. Kobayashi and M. Horibe, Tetrahedron: Asymmetry, 1995, 6, 2565; T. Mukaiyama, Aldrichim. Acta, 1996, 29, 59, and references cited therein; M. Asami and S. Inoue, Bull. Chem. Soc. Jpn., 1997, 79, 1687.
2. S. Kobayashi and T. Mukaiyama, Chem. Lett., 1989, 297; S. Kobayashi, H. Uchiro, Y. Fujishita, I. Shiina and T. Mukaiyama, J. Am. Chem. Soc., 1991, 113, 4247; S. Kobayashi and M. Horibe, J. Am. Chem. Soc., 1994, 116, 9805; S. Kobayashi and M. Horibe, Tetrahedron: Asymmetry, 1995, 6, 2565; T. Mukaiyama, Aldrichim. Acta, 1996, 29, 59, and references cited therein; M. Asami and S. Inoue, Bull. Chem. Soc. Jpn., 1997, 79, 1687.
3. S. Kobayashi and T. Mukaiyama, Chem. Lett., 1989, 297; S. Kobayashi, H. Uchiro, Y. Fujishita, I. Shiina and T. Mukaiyama, J. Am. Chem. Soc., 1991, 113, 4247; S. Kobayashi and M. Horibe, J. Am. Chem. Soc., 1994, 116, 9805; S. Kobayashi and M. Horibe, Tetrahedron: Asymmetry, 1995, 6, 2565; T. Mukaiyama, Aldrichim. Acta, 1996, 29, 59, and references cited therein; M. Asami and S. Inoue, Bull. Chem. Soc. Jpn., 1997, 79, 1687.
4. S. Kobayashi and T. Mukaiyama, Chem. Lett., 1989, 297; S. Kobayashi, H. Uchiro, Y. Fujishita, I. Shiina and T. Mukaiyama, J. Am. Chem. Soc., 1991, 113, 4247; S. Kobayashi and M. Horibe, J. Am. Chem. Soc., 1994, 116, 9805; S. Kobayashi and M. Horibe, Tetrahedron: Asymmetry, 1995, 6, 2565; T. Mukaiyama, Aldrichim. Acta, 1996, 29, 59, and references cited therein; M. Asami and S. Inoue, Bull. Chem. Soc. Jpn., 1997, 79, 1687.
5. S. Kobayashi and T. Mukaiyama, Chem. Lett., 1989, 297; S. Kobayashi, H. Uchiro, Y. Fujishita, I. Shiina and T. Mukaiyama, J. Am. Chem. Soc., 1991, 113, 4247; S. Kobayashi and M. Horibe, J. Am. Chem. Soc., 1994, 116, 9805; S. Kobayashi and M. Horibe, Tetrahedron: Asymmetry, 1995, 6, 2565; T. Mukaiyama, Aldrichim. Acta, 1996, 29, 59, and references cited therein; M. Asami and S. Inoue, Bull. Chem. Soc. Jpn., 1997, 79, 1687.
6. S. Kobayashi and T. Mukaiyama, Chem. Lett., 1989, 297; S. Kobayashi, H. Uchiro, Y. Fujishita, I. Shiina and T. Mukaiyama, J. Am. Chem. Soc., 1991, 113, 4247; S. Kobayashi and M. Horibe, J. Am. Chem. Soc., 1994, 116, 9805; S. Kobayashi and M. Horibe, Tetrahedron: Asymmetry, 1995, 6, 2565; T. Mukaiyama, Aldrichim. Acta, 1996, 29, 59, and references cited therein; M. Asami and S. Inoue, Bull. Chem. Soc. Jpn., 1997, 79, 1687.
7. T. Oriyama, Y. Hori, K. Imai, and R. Sasaki, Tetrahedron Lett., 1996, 37, 8543; T. Oriyama, K. Imai, T. Hosoya, and T. Sano, Tetrahedron Lett., 1998, 39, 397; T. Oriyama, K. Imai, T. Sano, and T. Hosoya, Tetrahedron Lett., 1998, 39, 3529; T. Sano, K. Imai, K. Ohashi, and T. Oriyama, Chem. Lett., 1999, 265.
8. T. Oriyama, Y. Hori, K. Imai, and R. Sasaki, Tetrahedron Lett., 1996, 37, 8543; T. Oriyama, K. Imai, T. Hosoya, and T. Sano, Tetrahedron Lett., 1998, 39, 397; T. Oriyama, K. Imai, T. Sano, and T. Hosoya, Tetrahedron Lett., 1998, 39, 3529; T. Sano, K. Imai, K. Ohashi, and T. Oriyama, Chem. Lett., 1999, 265.
9. T. Oriyama, Y. Hori, K. Imai, and R. Sasaki, Tetrahedron Lett., 1996, 37, 8543; T. Oriyama, K. Imai, T. Hosoya, and T. Sano, Tetrahedron Lett., 1998, 39, 397; T. Oriyama, K. Imai, T. Sano, and T. Hosoya, Tetrahedron Lett., 1998, 39, 3529; T. Sano, K. Imai, K. Ohashi, and T. Oriyama, Chem. Lett., 1999, 265.
10. T. Oriyama, Y. Hori, K. Imai, and R. Sasaki, Tetrahedron Lett., 1996, 37, 8543; T. Oriyama, K. Imai, T. Hosoya, and T. Sano, Tetrahedron Lett., 1998, 39, 397; T. Oriyama, K. Imai, T. Sano, and T. Hosoya, Tetrahedron Lett., 1998, 39, 3529; T. Sano, K. Imai, K. Ohashi, and T. Oriyama, Chem. Lett., 1999, 265.
11. M. A. Abreo, N.-H. Ling, D. S. Garvey, D. E. Gunn, A.-M. Hettinger, J. T. Wasicak, P. A. Pavlik, Y. C. Martin, D. L. Donnelly-Roberts, D. J. Anderson, J. P. Sullivan, M. Williams, S. P. Arneric, and M. W. Holladay, J. Med. Chem., 1996, 39, 817; M. W. Holladay, J. T. Wasicak, N.-H. Lin, Y. He, K. B. Ryther, A. W. Bannon, M. J. Buckley, D. J. B. Kim, D. J. Anderson, J. E. Campbell, T. A. Kuntzweiler, D. L. Donnelly-Roberts, M. Piattoni-Kaplan, C. A. Briggs, M. Williams, and S. Arneric, J. Med. Chem., 1998, 41, 407.
12. M. A. Abreo, N.-H. Ling, D. S. Garvey, D. E. Gunn, A.-M. Hettinger, J. T. Wasicak, P. A. Pavlik, Y. C. Martin, D. L. Donnelly-Roberts, D. J. Anderson, J. P. Sullivan, M. Williams, S. P. Arneric, and M. W. Holladay, J. Med. Chem., 1996, 39, 817; M. W. Holladay, J. T. Wasicak, N.-H. Lin, Y. He, K. B. Ryther, A. W. Bannon, M. J. Buckley, D. J. B. Kim, D. J. Anderson, J. E. Campbell, T. A. Kuntzweiler, D. L. Donnelly-Roberts, M. Piattoni-Kaplan, C. A. Briggs, M. Williams, and S. Arneric, J. Med. Chem., 1998, 41, 407.
13. B. Cardillo, R. Galeazzi, G. Mobbili, and M. Orena, Synlett, 1995, 1159;
14. R. Galeazzi, G. Mobbili, and M. Orena, Tetrahedron, 1996, 52, 1069;
15. R. Galeazzi, G. Mobbili, and M. Orena, Tetrahedron: Asymmetry, 1997, 8, 133.
16. B. V. Yang, D. O'Rourke, and J. Li, Synlett, 1993, 195.