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Volumn 2015, Issue 18, 2015, Pages 3894-3898

Peptide‐Catalyzed Desymmetrization of an Achiral Ferrocenyl Compound To Induce Planar Chirality

Author keywords

Asymmetric catalysis; Desymmetrization; Organocatalysis; Peptides; Planar chirality

Indexed keywords


EID: 85027943769     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201500428     Document Type: Article
Times cited : (12)

References (87)
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    • For reviews of planar‐chiral ligands for metal catalysts, see:.
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    • For reviews of planar‐chiral organocatalysts, see:.
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    • For recent selected examples, see:
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    • For a recent excellent review, see:
    • For a recent excellent review, see:.
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    • For examples of synthesizing planar‐chiral compounds with organocatalysts, see:
    • For examples of synthesizing planar‐chiral compounds with organocatalysts, see:.
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    • For reviews of peptide catalysts, see:
    • For reviews of peptide catalysts, see:.
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    • Rios, R., Molecules 14 (2009), 4747–4758.
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    • .
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    • For reviews of organocatalytic transfer hydrogenation with Hantzsch esters, see:
    • For reviews of organocatalytic transfer hydrogenation with Hantzsch esters, see:.
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    • 85128606684 scopus 로고    scopus 로고
    • For an example of a similar reaction sequence, see:
    • For an example of a similar reaction sequence, see:.
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    • .
  • 80
    • 85128637545 scopus 로고    scopus 로고
    • The ratio of product 5 and other diastereomers was estimated to be 87:13 by 1H NMR spectroscopy.
    • The ratio of product 5 and other diastereomers was estimated to be 87:13 by 1H NMR spectroscopy.
  • 81
    • 85128631182 scopus 로고    scopus 로고
    • One of the major diastereomers was assigned as the one with a rel‐(4R,5S,Sp) configuration, while compound 5 was assigned rel‐(4R,5S,Rp). Two other diastereomers were found in the crude mixture, but the stereostructures were not determined. The ratio of product 5 and diastereomers was estimated to be 66:34.
    • One of the major diastereomers was assigned as the one with a rel‐(4R,5S,Sp) configuration, while compound 5 was assigned rel‐(4R,5S,Rp). Two other diastereomers were found in the crude mixture, but the stereostructures were not determined. The ratio of product 5 and diastereomers was estimated to be 66:34.
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    • In some cases, this type of intramolecular cyclization is performed in the presence of benzoic acid, see:
    • In some cases, this type of intramolecular cyclization is performed in the presence of benzoic acid, see:.
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    • See Scheme S1 in the Supporting Information.
    • See Scheme S1 in the Supporting Information.
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    • 85128669332 scopus 로고    scopus 로고
    • For possible models of enamine intermediates, see Scheme S2 in the Supporting Information.
    • For possible models of enamine intermediates, see Scheme S2 in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.