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Volumn 10, Issue 23, 2008, Pages 5497-5499

Silver ion-induced grob fragmentation of γ-amino iodides: Highly stereoselective synthesis of polysubstituted piperidines

Author keywords

[No Author keywords available]

Indexed keywords

IODIDE; PIPERIDINE; PIPERIDINE DERIVATIVE; SILVER;

EID: 61349190967     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8024605     Document Type: Article
Times cited : (20)

References (37)
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    • Buffat, M.G.P.1
  • 12
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    • For other recent stereoselective synthesis of substituted piperidines, see: e
    • For other recent stereoselective synthesis of substituted piperidines, see: (e) Hayashi, Y.; Gotoh, H.; Masui, R.; Ishikawa, H. Angew. Chem., Int. Ed. 2008, 47, 4012.
    • (2008) Angew. Chem., Int. Ed , vol.47 , pp. 4012
    • Hayashi, Y.1    Gotoh, H.2    Masui, R.3    Ishikawa, H.4
  • 19
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    • and references therein
    • (a) Larivée, A.; Charette, A. B. Org. Lett. 2006, 8, 3955, and references therein.
    • (2006) Org. Lett , vol.8 , pp. 3955
    • Larivée, A.1    Charette, A.B.2
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    • 61349139216 scopus 로고    scopus 로고
    • See the Supporting Information for more details
    • See the Supporting Information for more details.
  • 25
    • 38349043789 scopus 로고    scopus 로고
    • For the chemoselective reduction of tertiary amides, see
    • For the chemoselective reduction of tertiary amides, see: Barbe, G.; Charette, A. B. J. Am. Chem. Soc. 2008, 130, 18.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 18
    • Barbe, G.1    Charette, A.B.2
  • 30
    • 0001190506 scopus 로고
    • Alkoxide: a
    • Alkoxide: (a) Wharton, P. S. J. Org. Chem. 1961, 26, 4781.
    • (1961) J. Org. Chem , vol.26 , pp. 4781
    • Wharton, P.S.1
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    • For recent synthetic applications, see: d
    • For recent synthetic applications, see: (d) Larionov, O. V.; Corey, E. J. J. Am. Chem. Soc. 2008, 130, 2954.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 2954
    • Larionov, O.V.1    Corey, E.J.2
  • 35
    • 61349193008 scopus 로고    scopus 로고
    • Most amines in this paper have been purified using our recently reported, silica gel chromatography free procedures. See refs 7 and 8 for more details
    • Most amines in this paper have been purified using our recently reported, silica gel chromatography free procedures. See refs 7 and 8 for more details.
  • 36
    • 61349088425 scopus 로고    scopus 로고
    • Enantiomeric purity was determined by SFC using chiral stationary phases. See the Supporting Information for more details, Chemical Equation Presented
    • Enantiomeric purity was determined by SFC using chiral stationary phases. See the Supporting Information for more details. (Chemical Equation Presented)
  • 37
    • 0037042279 scopus 로고    scopus 로고
    • At the present time, we cannot rule out the formation of a carbocation at C-α followed by a fragmentation that is faster than C-C bond rotation. However, we believe that the formation of a primary carbocation under these conditions is unlikely. For recent calculations, see: Alder, R. W, Harvey, J. N, Oakley, M. T. J. Am. Chem. Soc. 2002, 124, 4960
    • At the present time, we cannot rule out the formation of a carbocation at C-α followed by a fragmentation that is faster than C-C bond rotation. However, we believe that the formation of a primary carbocation under these conditions is unlikely. For recent calculations, see: Alder, R. W.; Harvey, J. N.; Oakley, M. T. J. Am. Chem. Soc. 2002, 124, 4960.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.