Studies on the structure-enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation reaction of α-diazo-β-keto sulfones possessing a methyl-substituted phenyl group

Hiroyuki Takeda, Masahisa Nakada

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    26 Citations (Scopus)

    Abstract

    This manuscript describes studies on structure-enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation (IMCP) reaction of α-diazo-β-keto sulfones possessing a methyl-substituted phenyl group. Enantioselectivity of the IMCP reaction of the α-diazo-β-keto sulfones was varied by the position of a methyl group on the phenyl group in the substrate, and the 2,3-dimethylphenyl sulfone 11h provided the product 12h in 95% yield with 93% ee. This yield is superior to that of the substrate with a mesityl sulfone 11b, and the product 12h is useful because alkylation of its cyclopropane-opened β-keto sulfone derivative 15h provides the C-alkylated product as a major product.

    Original languageEnglish
    Pages (from-to)2896-2906
    Number of pages11
    JournalTetrahedron Asymmetry
    Volume17
    Issue number20
    DOIs
    Publication statusPublished - 2006 Nov 6

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    Sulfones
    sulfones
    Enantioselectivity
    Alkylation
    Substrates
    products
    Derivatives
    cyclopropane
    alkylation

    ASJC Scopus subject areas

    • Inorganic Chemistry
    • Organic Chemistry
    • Materials Chemistry
    • Drug Discovery

    Cite this

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    abstract = "This manuscript describes studies on structure-enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation (IMCP) reaction of α-diazo-β-keto sulfones possessing a methyl-substituted phenyl group. Enantioselectivity of the IMCP reaction of the α-diazo-β-keto sulfones was varied by the position of a methyl group on the phenyl group in the substrate, and the 2,3-dimethylphenyl sulfone 11h provided the product 12h in 95{\%} yield with 93{\%} ee. This yield is superior to that of the substrate with a mesityl sulfone 11b, and the product 12h is useful because alkylation of its cyclopropane-opened β-keto sulfone derivative 15h provides the C-alkylated product as a major product.",
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