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Volumn 132, Issue 43, 2010, Pages 15185-15191

Catalytic asymmetric synthesis of chiral allylic esters

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALCOHOL; ASYMMETRIC SYNTHESIS; CYCLOPENTADIENYLS; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; IN-SITU;

EID: 78049390669     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja106685w     Document Type: Article
Times cited : (61)

References (75)
  • 1
    • 78049409183 scopus 로고    scopus 로고
    • Enantioenriched allylic esters are ubiquitous intermediates in the synthesis of complex molecules. Selected recent examples include the following
    • Enantioenriched allylic esters are ubiquitous intermediates in the synthesis of complex molecules. Selected recent examples include the following:
  • 5
    • 78049369363 scopus 로고    scopus 로고
    • For a comprehensive review of the synthesis of allylic alcohols, see
    • For a comprehensive review of the synthesis of allylic alcohols, see
  • 7
    • 78049368579 scopus 로고    scopus 로고
    • Enzymatic kinetic resolution
    • Enzymatic kinetic resolution
  • 12
    • 78049375823 scopus 로고    scopus 로고
    • Palladium-catalyzed kinetic resolution
    • Palladium-catalyzed kinetic resolution
  • 22
    • 78049414444 scopus 로고    scopus 로고
    • A novel catalytic asymmetric approach involving Cu-catalyzed catalytic asymmetric allylic alkylation was described recently
    • A novel catalytic asymmetric approach involving Cu-catalyzed catalytic asymmetric allylic alkylation was described recently
  • 26
    • 78049405577 scopus 로고    scopus 로고
    • For comprehensive reviews see
    • For comprehensive reviews see
  • 29
    • 78049385985 scopus 로고    scopus 로고
    • Direct palladium-catalyzed allylic C-H oxidation to provide 3-acyloxy-1-alkenes in modest enantioselectivity has been reported by the White group
    • Direct palladium-catalyzed allylic C-H oxidation to provide 3-acyloxy-1-alkenes in modest enantioselectivity has been reported by the White group
  • 40
    • 78049360897 scopus 로고    scopus 로고
    • For a recent review of enantioselective allylation reactions, see
    • For a recent review of enantioselective allylation reactions, see
  • 42
    • 78049357221 scopus 로고    scopus 로고
    • For a recent review, see
    • For a recent review, see
  • 50
    • 78049377270 scopus 로고    scopus 로고
    • J. Am. Chem. Soc. 2010, http://dx.doi.org/10.1021/ja106688j, following paper in this issue
    • Cannon, J., Kirsch, S. F., Overman, L. E., and Sneddon, H. F. J. Am. Chem. Soc. 2010, 132, http://dx.doi.org/10.1021/ja106688j, following paper in this issue.
    • , vol.132
    • Cannon, J.1    Kirsch, S.F.2    Overman, L.E.3    Sneddon, H.F.4
  • 52
    • 78049368296 scopus 로고    scopus 로고
    • Cationic complexes were generated from chloride-bridged dimer precursors by pretreatment at room temperature with 4 equiv of the silver salt specified in Figure 1
    • Cationic complexes were generated from chloride-bridged dimer precursors by pretreatment at room temperature with 4 equiv of the silver salt specified in Figure 1.
  • 53
    • 78049372617 scopus 로고    scopus 로고
    • A negative sign before the % ee indicates that ent - 4b was produced in excess
    • A negative sign before the % ee indicates that ent-4b was produced in excess.
  • 60
    • 78049390816 scopus 로고    scopus 로고
    • a = 12.8; calculated using Advanced Chemistry Development (ACD/Labs) Software, version 8.14
    • a = 12.8; calculated using Advanced Chemistry Development (ACD/Labs) Software, version 8.14.
  • 63
    • 78049376833 scopus 로고    scopus 로고
    • Under identical conditions, allylic trichloroacetamide is not detected in the corresponding reaction of (Z)-imidate 3b
    • Under identical conditions, allylic trichloroacetamide is not detected in the corresponding reaction of (Z)-imidate 3b.
  • 64
    • 78049387302 scopus 로고    scopus 로고
    • This result is not surprising in light of the rapid interconversion of catalysts 2 and 14 in the presence of acetic acid
    • This result is not surprising in light of the rapid interconversion of catalysts 2 and 14 in the presence of acetic acid.
  • 68
    • 78049385076 scopus 로고    scopus 로고
    • None of the reactions reported in Table 4 were homogeneous
    • None of the reactions reported in Table 4 were homogeneous.
  • 69
    • 78049403735 scopus 로고    scopus 로고
    • In the absence of catalyst 2, reaction of 3e with o -chlorobenzoic acid provided ∼20% conversion to the linear o -chlorobenzoate ester after 24 h
    • In the absence of catalyst 2, reaction of 3e with o -chlorobenzoic acid provided ∼20% conversion to the linear o -chlorobenzoate ester after 24 h.
  • 72
    • 78049385398 scopus 로고    scopus 로고
    • 2 (2) at room temperature. However, this reaction is low yielding because the catalyst becomes poisoned, presumably from the formation of a minor byproduct
    • 2 (2) at room temperature. However, this reaction is low yielding because the catalyst becomes poisoned, presumably from the formation of a minor byproduct.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.