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Volumn 39, Issue 1-2, 1998, Pages 105-108

Conformationally interlocked amides: Remote asymmetric induction by mechanical transfer of stereochemical information

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMIDE;

EID: 0031974101     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10443-9     Document Type: Article
Times cited : (64)

References (33)
  • 11
    • 0002999412 scopus 로고
    • Atropisomers are conformational isomers which can exist as discrete compounds. For a definition, see
    • Atropisomers are conformational isomers which can exist as discrete compounds. For a definition, see Oki, M. Topics in Stereochem. 1983, 14, 1.
    • (1983) Topics in Stereochem , vol.14 , pp. 1
    • Oki, M.1
  • 22
    • 0029874183 scopus 로고    scopus 로고
    • In our N,N-diisopropylbenzamides, competition always favours lateral lithiation over ortholithiation. See
    • In our N,N-diisopropylbenzamides, competition always favours lateral lithiation over ortholithiation. See Court, J.J.; Hlasta, D. J. Tetrahedron Lett. 1996, 37, 1335.
    • (1996) J. Tetrahedron Lett. , vol.37 , pp. 1335
    • Court, J.J.1    Hlasta, D.2
  • 23
    • 0344518613 scopus 로고    scopus 로고
    • Conformations of 5 and 7 were studied using Macromodel/MM2*
    • Conformations of 5 and 7 were studied using Macromodel/MM2*.
  • 25
    • 0345380867 scopus 로고    scopus 로고
    • Diastereoselectivity was assessed by analytical HPLC of the crude reaction mixture, and was >97:3.
    • Diastereoselectivity was assessed by analytical HPLC of the crude reaction mixture, and was >97:3.
  • 26
    • 0344518614 scopus 로고    scopus 로고
    • note
    • That 9 is a meso compound tells us nothing about the conformation of the non-chirotopic stereogenic axis. Our assignment of syn,syn stereochemistry is based on precedent in the naphthamide series, along with the fact that no epimerisation to the other meso diastereoisomer was observed on heating this compound at 55°C for 24 h. Note that the stereochemistry of 9, unlike that of a superficially similar compound in , originates by 1,5-transmission of stereochemical information from one centre to the other, and not from the stereogenic axis by two-way 1,4-asymmetric induction.
  • 28


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.