Development of catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfones and applications to natural product synthesis

Masahiro Honma, Hiroyuki Takeda, Masashi Takano, Masahisa Nakada

    Research output: Contribution to journalArticle

    40 Citations (Scopus)

    Abstract

    The catalytic asymmetric intramolecular cyclopropanation (CAIMCP) of α-diazo-β-keto sulfones developed in our laboratory and applications to the total synthesis of natural products are described. CAIMCP features (a) a wide applicability, not only to the preparation of bicyclo[n.1.0]alkanes and tricyclo[4.n.0.0]alkenes, but also to the enantioselective total synthesis of natural products, (b) the formation of highly crystalline products, which facilitate the production of enantiomerically pure synthetic intermediates, and (c) the generation of products with a variety of functionalities, such as cyclopropane, ketone, and sulfone, beneficial to the total synthesis of natural products.

    Original languageEnglish
    Pages (from-to)1695-1712
    Number of pages18
    JournalSynlett
    Issue number11
    DOIs
    Publication statusPublished - 2009 Jul

    Fingerprint

    Sulfones
    Biological Products
    Alkanes
    Alkenes
    Ketones
    Crystalline materials

    Keywords

    • Asymmetric catalysis
    • Carbene complexes
    • Diazo compounds
    • Natural products
    • Sulfones

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Development of catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfones and applications to natural product synthesis. / Honma, Masahiro; Takeda, Hiroyuki; Takano, Masashi; Nakada, Masahisa.

    In: Synlett, No. 11, 07.2009, p. 1695-1712.

    Research output: Contribution to journalArticle

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