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Volumn 30, Issue 12, 1991, Pages 1690-1693

Stereoselective Synthesis of Cyclic Dipeptide Hydroxyalkyl Isosteres via Metalated N,N‐Dialkylcarbamate 2‐Alkenyl Esters

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Indexed keywords


EID: 33748237495     PISSN: 05700833     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.199116901     Document Type: Article
Times cited : (12)

References (56)
  • 2
    • 84990072891 scopus 로고
    • in Comprehensive Medicinal Chemistry, Bd. 2, Pergamon, p. 391.
    • (1990)
    • Rich, D.H.1
  • 25
    • 0000163012 scopus 로고
    • Die Homoaldol-Reaktion oder wie man Probleme der Regio- und Stereoselektivität in den Griff bekommt
    • (1984) Angewandte Chemie , vol.96 , pp. 930
    • Hoppe, D.1
  • 30
    • 84990079688 scopus 로고    scopus 로고
    • Apparently with no exception, (E)‐2‐alkenyl carbamates give exclusively (Z)‐anti diastereomeres under these conditions [8].
  • 31
    • 84990099232 scopus 로고    scopus 로고
    • 13C NMR spectra are in agreement with the proposed structures, although their significance is limited by line broadening. The new compounds gave satisfactory microanalyses (C, H ± 0.3 %).
  • 32
    • 84990139076 scopus 로고    scopus 로고
    • 2): 21, −32.7; 16, −75.0; 22, −57.0.
  • 33
    • 84990124949 scopus 로고    scopus 로고
    • 2): m.p. 149 °C (hexane) was obtained.
  • 44
    • 84990072015 scopus 로고    scopus 로고
    • 2O/HOAc 10:1) in THF gave 9a in 90 % yield but no silylated acid.
  • 49
    • 84990089026 scopus 로고    scopus 로고
    • 3 to yield 9c in 92% yield after chromatography.
  • 50
    • 84990089013 scopus 로고    scopus 로고
    • The concentration of 12a should not exceed 0.03 M and the reaction time should not exceed 20 min to avoid the formation of side products.
  • 51
    • 84990161805 scopus 로고    scopus 로고
    • 2 should be 0.03 M.
  • 52
    • 84990102853 scopus 로고    scopus 로고
    • The reaction was quenched at −76 °C with HOAc prior to workup.
  • 53
    • 84990161807 scopus 로고    scopus 로고
    • The reaction was quenched at −40 °C with HOAc prior to workup.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.