Asymmetric catalysis of intramolecular cyclopropanation of 5-aryl-1-diazo-1-mesitylsulfonyl-5-hexen-2-ones

Takashi Sawada, Masahisa Nakada

    Research output: Contribution to journalArticle

    42 Citations (Scopus)

    Abstract

    We have examined the catalytic asymmetric intramolecular cyclopropanation (IMCP) reactions of 5-aryl-1-diazo-1-mesitylsulfonyl-5-hexen-2-ones, and found that the substituent of the 5-aryl group dramatically changes the enantioselectivity. That is, no enantioselectivity was observed when the substituent was a methoxy group; however, enantioselectivity was moderate when the substituent was a methylenedioxy group or a tert-butyldimethylsilyloxy group, and it dramatically increased when the substituent was lacking (96% ee) or a benzoyloxy group (93% ee).

    Original languageEnglish
    Pages (from-to)1527-1532
    Number of pages6
    JournalAdvanced Synthesis and Catalysis
    Volume347
    Issue number11-13
    DOIs
    Publication statusPublished - 2005 Oct

    Fingerprint

    Enantioselectivity
    Catalysis

    Keywords

    • Asymmetric catalysis
    • Cyclization
    • Cyclopropanes
    • Diazo compounds
    • Enantioselectivity

    ASJC Scopus subject areas

    • Chemistry (miscellaneous)
    • Organic Chemistry
    • Catalysis

    Cite this

    Asymmetric catalysis of intramolecular cyclopropanation of 5-aryl-1-diazo-1-mesitylsulfonyl-5-hexen-2-ones. / Sawada, Takashi; Nakada, Masahisa.

    In: Advanced Synthesis and Catalysis, Vol. 347, No. 11-13, 10.2005, p. 1527-1532.

    Research output: Contribution to journalArticle

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