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Volumn , Issue 27, 2007, Pages 4517-4524

On the synthesis and reactivity of enantiopure azetidines

Author keywords

Amino alcohols; Azetidines; Bromocyclization; Cyclization; Vinyl bromide; Vinylsilane

Indexed keywords


EID: 34748832396     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700283     Document Type: Article
Times cited : (18)

References (60)
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    • For recent examples of O-cyclizations, see: a G. Fragale, T. Wirth, Eur. J. Org. Chem. 1998, 1361;
    • For recent examples of O-cyclizations, see: a) G. Fragale, T. Wirth, Eur. J. Org. Chem. 1998, 1361;
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    • For recent examples of N-cyclizations, see: a N. De Kimpe, D. De Smaele, J. Heterocycl. Chem. 2000, 37, 607;
    • For recent examples of N-cyclizations, see: a) N. De Kimpe, D. De Smaele, J. Heterocycl. Chem. 2000, 37, 607;
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    • For examples of silicon-directed O-cyclizations, see: a K. Miura, T. Hondo, H. Saito, H. Ito, A. Hosomi, J. Org. Chem. 1997, 62, 8292;
    • For examples of silicon-directed O-cyclizations, see: a) K. Miura, T. Hondo, H. Saito, H. Ito, A. Hosomi, J. Org. Chem. 1997, 62, 8292;
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    • For examples of silicon-directed N-cyclizations, see: a K. Miura, T. Hondo, T. Nakagawa, T. Takahashi, A. Hosomi, Org. Lett. 2000, 2, 385;
    • For examples of silicon-directed N-cyclizations, see: a) K. Miura, T. Hondo, T. Nakagawa, T. Takahashi, A. Hosomi, Org. Lett. 2000, 2, 385;
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    • Preliminary communication: V. Lemau de Talancé, E. Banide, B. Bertin, S. Comesse, C. Kadouri-Puchot, Tetrahedron Lett. 2005, 46, 8023.
    • Preliminary communication: V. Lemau de Talancé, E. Banide, B. Bertin, S. Comesse, C. Kadouri-Puchot, Tetrahedron Lett. 2005, 46, 8023.
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    • For reviews, see: a, Eds, A. Padwa, Elsevier, Oxford, chapter 1.18, pp
    • For reviews, see: a) N. De Kimpe, in Comprehensive Heterocyclic Chemistry II (Eds.: A. Padwa), Elsevier, Oxford, 1996, vol. 1B, chapter 1.18, pp. 507-589;
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.1 B , pp. 507-589
    • De Kimpe, N.1
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    • 34748910606 scopus 로고    scopus 로고
    • This solvent was already reported as the more efficient solvent for a 4-exo trig process: ref.[2b,2h
    • [2b,2h]
  • 47
    • 34748831638 scopus 로고    scopus 로고
    • [13] as implemented in the AMPAC program version 4.0 QCPE No527. The geometries were optimized by using the Davidson-Fletcher-Powell algorithm (FLEPO procedure) that minimizes the energy with respect to all internal coordinates
    • [13] as implemented in the AMPAC program version 4.0 QCPE No527. The geometries were optimized by using the Davidson-Fletcher-Powell algorithm (FLEPO procedure) that minimizes the energy with respect to all internal coordinates.
  • 50
    • 34748850674 scopus 로고    scopus 로고
    • These calculations excluded any other configuration for the nitrogen atom. Any attempt at optimisation led to the stable configuration proposed here
    • These calculations excluded any other configuration for the nitrogen atom. Any attempt at optimisation led to the stable configuration proposed here.
  • 51
    • 34748842596 scopus 로고    scopus 로고
    • [17], α-halo azetidines are known to be unstable and rearrange to pyrrolidines: (Chemical Equation Presented)
    • [17], α-halo azetidines are known to be unstable and rearrange to pyrrolidines: (Chemical Equation Presented)
  • 54
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    • The (Z) configuration was based upon the coupling (7.0 Hz) of the ethylene hydrogen atoms.
    • The (Z) configuration was based upon the coupling (7.0 Hz) of the ethylene hydrogen atoms.
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    • For an anti elimination of β-silyl azides, see: L. Chabaud, Y. Landais, Tetrahedron Lett. 2003, 44, 6995.
    • For an anti elimination of β-silyl azides, see: L. Chabaud, Y. Landais, Tetrahedron Lett. 2003, 44, 6995.
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    • For references concerning the utility of vinylsilanes as intermediates in the stereoselective synthesis of vinyl halides, see: a M. A. Brook, M. A. Hadi, A. Neuy, J. Chem. Soc. Chem. Commun. 1989, 957;
    • For references concerning the utility of vinylsilanes as intermediates in the stereoselective synthesis of vinyl halides, see: a) M. A. Brook, M. A. Hadi, A. Neuy, J. Chem. Soc. Chem. Commun. 1989, 957;
  • 59
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    • For an example of the ring opening of azetidinium ions by a β-elimination, see
    • For an example of the ring opening of azetidinium ions by a β-elimination, see: G. Gionta, C. Lillocci, J. Phys. Org. Chem. 1993, 6, 187.
    • (1993) J. Phys. Org. Chem , vol.6 , pp. 187
    • Gionta, G.1    Lillocci, C.2
  • 60
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    • N2′ ring opening of four-membered cyclic ammonium ions, see: F. Couty, F. Durrat, G. Evano, J. Marrot, Eur. J. Org. Chem. 2006, 4214.
    • N2′ ring opening of four-membered cyclic ammonium ions, see: F. Couty, F. Durrat, G. Evano, J. Marrot, Eur. J. Org. Chem. 2006, 4214.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.