메뉴 건너뛰기




Volumn 12, Issue 8, 2010, Pages 1668-1671

Stereoselective synthesis of trisubstituted aziridines with N -α-diazoacyl camphorsultam

Author keywords

[No Author keywords available]

Indexed keywords


EID: 77951146759     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100104v     Document Type: Article
Times cited : (40)

References (46)
  • 10
    • 77951150328 scopus 로고    scopus 로고
    • For other chiral Lewis acid-catalyzed reactions, see
    • For other chiral Lewis acid-catalyzed reactions, see
  • 18
    • 77951194725 scopus 로고    scopus 로고
    • For asymmetric aziridination with diazoalkanes and imines mediated by chiral sulfur ylides, see
    • For asymmetric aziridination with diazoalkanes and imines mediated by chiral sulfur ylides, see
  • 25
    • 77951174747 scopus 로고    scopus 로고
    • For the use of α-substituted α-diazocarbonyl compounds in acid-catalyzed stereoselective synthesis, see
    • For the use of α-substituted α-diazocarbonyl compounds in acid-catalyzed stereoselective synthesis, see
  • 32
    • 77951202916 scopus 로고    scopus 로고
    • 1H NMR of the crude material in small quantities which could be easily removed by column chromatography on silica gel.
    • 1H NMR of the crude material in small quantities which could be easily removed by column chromatography on silica gel.
  • 33
    • 77951149717 scopus 로고    scopus 로고
    • A catalytic amount of camphorsulfonic acid indeed facilitated the reaction of 1b and N -Boc imine smoothly, although the aziridine was obtained in a racemic form. In our preliminary experiments, neither chiral phosphoric acid nor dicarboxylic acid (see refs 6 and 7) promoted the reaction even at room temperature.
    • A catalytic amount of camphorsulfonic acid indeed facilitated the reaction of 1b and N -Boc imine smoothly, although the aziridine was obtained in a racemic form. In our preliminary experiments, neither chiral phosphoric acid nor dicarboxylic acid (see refs 6 and 7) promoted the reaction even at room temperature.
  • 34
    • 77951154307 scopus 로고    scopus 로고
    • For reviews on Brønsted acid catalysis, see
    • For reviews on Brønsted acid catalysis, see
  • 38
    • 77951183484 scopus 로고    scopus 로고
    • The reaction provided a mixture of the corresponding aziridine, oxazolidin-2-one, and 2-benzyloxyoxazoline.
    • The reaction provided a mixture of the corresponding aziridine, oxazolidin-2-one, and 2-benzyloxyoxazoline.
  • 41
    • 77951160029 scopus 로고    scopus 로고
    • For recent reviews on asymmetric synthesis of α,α- disubstituted α-Amino acids, see
    • For recent reviews on asymmetric synthesis of α,α- disubstituted α-amino acids, see
  • 46
    • 77951158354 scopus 로고    scopus 로고
    • CCDC 710136 (3a) and CCDC 750124 (6) contain the supplementary crystallographic data for this paper. The crystallographic coordinates have been deposited with the Cambridge Crystallographic Data Centre; deposition nos. 710136 and 750124. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/conts/retrieving.html.
    • CCDC 710136 (3a) and CCDC 750124 (6) contain the supplementary crystallographic data for this paper. The crystallographic coordinates have been deposited with the Cambridge Crystallographic Data Centre; deposition nos. 710136 and 750124. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/conts/retrieving.html.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.