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Volumn 61, Issue 19, 1996, Pages 6700-6705

Asymmetric synthesis. 39. Synthesis of 2-(1-aminoalkyl)piperidines via 2-cyano-6-phenyl oxazolopiperidine

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE;

EID: 0029848930     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960910s     Document Type: Article
Times cited : (35)

References (32)
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    • For recent exemples of synthesis of biologically active compounds, see: (a) Naylor, A.; Judd, D. B.; Scopes, D. I. C.; Hayes, A. G.; Birch, P. J. J. Med. Chem. 1994, 37, 2138. (b) Giardina, G.; Clarke, G. D.; Dondio, G.; Petrone, G.; Sbacchi, M.; Vecchietti, V. J. Med. Chem. 1994, 37, 3482. (c) Morikawa, K.; Honda, M.; Endoh, K.; Matsumoto, T.; Akamatsu, K.; Mitsui, H.; Koizumi, M. Chem. Pharm. Bull. 1990, 38, 930.
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  • 4
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    • For recent exemples of synthesis of biologically active compounds, see: (a) Naylor, A.; Judd, D. B.; Scopes, D. I. C.; Hayes, A. G.; Birch, P. J. J. Med. Chem. 1994, 37, 2138. (b) Giardina, G.; Clarke, G. D.; Dondio, G.; Petrone, G.; Sbacchi, M.; Vecchietti, V. J. Med. Chem. 1994, 37, 3482. (c) Morikawa, K.; Honda, M.; Endoh, K.; Matsumoto, T.; Akamatsu, K.; Mitsui, H.; Koizumi, M. Chem. Pharm. Bull. 1990, 38, 930.
    • (1994) J. Med. Chem. , vol.37 , pp. 3482
    • Giardina, G.1    Clarke, G.D.2    Dondio, G.3    Petrone, G.4    Sbacchi, M.5    Vecchietti, V.6
  • 5
    • 0025345253 scopus 로고
    • For recent exemples of synthesis of biologically active compounds, see: (a) Naylor, A.; Judd, D. B.; Scopes, D. I. C.; Hayes, A. G.; Birch, P. J. J. Med. Chem. 1994, 37, 2138. (b) Giardina, G.; Clarke, G. D.; Dondio, G.; Petrone, G.; Sbacchi, M.; Vecchietti, V. J. Med. Chem. 1994, 37, 3482. (c) Morikawa, K.; Honda, M.; Endoh, K.; Matsumoto, T.; Akamatsu, K.; Mitsui, H.; Koizumi, M. Chem. Pharm. Bull. 1990, 38, 930.
    • (1990) Chem. Pharm. Bull. , vol.38 , pp. 930
    • Morikawa, K.1    Honda, M.2    Endoh, K.3    Matsumoto, T.4    Akamatsu, K.5    Mitsui, H.6    Koizumi, M.7
  • 6
    • 0027381329 scopus 로고
    • For recent examples of use of 2-(aminomethyl)pyrrolidine and -piperidine derivatives in asymmetric synthesis, see: (a) Froelich, O.; Bonin, M.; Quirion, J.-C.; Husson, H.-P. Tetrahedron: Asymmetry 1993, 4, 2335. (b) Kobayashi, S.; Hayashi, T. J. Org. Chem. 1995, 60, 1098. (c) Asami, M.; Usui, K.; Higuchi, S.; Inoue, S. Chem. Lett. 1994, 297.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 2335
    • Froelich, O.1    Bonin, M.2    Quirion, J.-C.3    Husson, H.-P.4
  • 7
    • 0028898190 scopus 로고
    • For recent examples of use of 2-(aminomethyl)pyrrolidine and -piperidine derivatives in asymmetric synthesis, see: (a) Froelich, O.; Bonin, M.; Quirion, J.-C.; Husson, H.-P. Tetrahedron: Asymmetry 1993, 4, 2335. (b) Kobayashi, S.; Hayashi, T. J. Org. Chem. 1995, 60, 1098. (c) Asami, M.; Usui, K.; Higuchi, S.; Inoue, S. Chem. Lett. 1994, 297.
    • (1995) J. Org. Chem. , vol.60 , pp. 1098
    • Kobayashi, S.1    Hayashi, T.2
  • 8
    • 0002467991 scopus 로고
    • For recent examples of use of 2-(aminomethyl)pyrrolidine and -piperidine derivatives in asymmetric synthesis, see: (a) Froelich, O.; Bonin, M.; Quirion, J.-C.; Husson, H.-P. Tetrahedron: Asymmetry 1993, 4, 2335. (b) Kobayashi, S.; Hayashi, T. J. Org. Chem. 1995, 60, 1098. (c) Asami, M.; Usui, K.; Higuchi, S.; Inoue, S. Chem. Lett. 1994, 297.
    • (1994) Chem. Lett. , pp. 297
    • Asami, M.1    Usui, K.2    Higuchi, S.3    Inoue, S.4
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    • note
    • In order to make easier comparison of NMR data, the products are described with the numbering indicated for 2 in Scheme 1.
  • 23
    • 16044372368 scopus 로고
    • Thèse de Doctorat, Université de Paris-Sud, Orsay
    • Bonin, M., Thèse de Doctorat, Université de Paris-Sud, Orsay, 1986.
    • (1986)
    • Bonin, M.1
  • 24
    • 16044362024 scopus 로고
    • The imino-oxazolidine structure was first proposed: Delgado, A.; Mauleon, D. Synth. Commun. 1988, 18, 823. We reported the same type of structure in our first communication (ref 8).
    • (1988) Synth. Commun. , vol.18 , pp. 823
    • Delgado, A.1    Mauleon, D.2
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    • 0000064113 scopus 로고
    • Trost, B. M.; Fleming, I. Eds; Pergamon Press: New York
    • Brewster, J. H. in Comprehensive Organic Synthesis. Trost, B. M.; Fleming, I. Eds; Pergamon Press: New York, 1991; Vol. 8, p 211.
    • (1991) Comprehensive Organic Synthesis , vol.8 , pp. 211
    • Brewster, J.H.1
  • 30
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    • Rappoport, Z., Ed.; Interscience: New York
    • Schaeffer, F. C. in Chemistry of the Cyano Group; Rappoport, Z., Ed.; Interscience: New York, 1971; p 239.
    • (1971) Chemistry of the Cyano Group , pp. 239
    • Schaeffer, F.C.1


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