Catalytic asymmetric intramolecular cyclopropanation of 2-diazo-3-oxo-6-heptenoic acid esters

Hiroyuki Takeda, Masahiro Honma, Ryoji Ida, Takashi Sawada, Masahisa Nakada

    Research output: Contribution to journalArticle

    27 Citations (Scopus)

    Abstract

    This manuscript describes studies on the catalytic asymmetric intramolecular cyclopropanation (IMCP) of 2-diazo-3-oxo-6-heptenoic acid esters. The enantioselectivity depends on the bulkiness of the ester moiety, and the 2,6-di-tert-butyl-4-methylphenyl ester of 2-diazo-3-oxo-6-heptenoic acid provided the product with 78% ee, suggesting that the catalytic asymmetric IMCP of α-diazo-β-keto esters could be a key reaction for the enantioselective synthesis of natural products as well as artificial molecules.

    Original languageEnglish
    Pages (from-to)579-582
    Number of pages4
    JournalSynlett
    Issue number4
    DOIs
    Publication statusPublished - 2007 Mar 1

    Fingerprint

    Esters
    Acids
    Enantioselectivity
    Biological Products
    Molecules
    diazo-2

    Keywords

    • α-diazo-β-keto ester
    • Asymmetric catalysis
    • Cyclopropanation
    • Enantioselectivity
    • Intramolecular reaction

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Catalytic asymmetric intramolecular cyclopropanation of 2-diazo-3-oxo-6-heptenoic acid esters. / Takeda, Hiroyuki; Honma, Masahiro; Ida, Ryoji; Sawada, Takashi; Nakada, Masahisa.

    In: Synlett, No. 4, 01.03.2007, p. 579-582.

    Research output: Contribution to journalArticle

    Takeda, Hiroyuki ; Honma, Masahiro ; Ida, Ryoji ; Sawada, Takashi ; Nakada, Masahisa. / Catalytic asymmetric intramolecular cyclopropanation of 2-diazo-3-oxo-6-heptenoic acid esters. In: Synlett. 2007 ; No. 4. pp. 579-582.
    @article{7063d82c25544610866fac78af602293,
    title = "Catalytic asymmetric intramolecular cyclopropanation of 2-diazo-3-oxo-6-heptenoic acid esters",
    abstract = "This manuscript describes studies on the catalytic asymmetric intramolecular cyclopropanation (IMCP) of 2-diazo-3-oxo-6-heptenoic acid esters. The enantioselectivity depends on the bulkiness of the ester moiety, and the 2,6-di-tert-butyl-4-methylphenyl ester of 2-diazo-3-oxo-6-heptenoic acid provided the product with 78{\%} ee, suggesting that the catalytic asymmetric IMCP of α-diazo-β-keto esters could be a key reaction for the enantioselective synthesis of natural products as well as artificial molecules.",
    keywords = "α-diazo-β-keto ester, Asymmetric catalysis, Cyclopropanation, Enantioselectivity, Intramolecular reaction",
    author = "Hiroyuki Takeda and Masahiro Honma and Ryoji Ida and Takashi Sawada and Masahisa Nakada",
    year = "2007",
    month = "3",
    day = "1",
    doi = "10.1055/s-2007-967964",
    language = "English",
    pages = "579--582",
    journal = "Synlett",
    issn = "0936-5214",
    publisher = "Georg Thieme Verlag",
    number = "4",

    }

    TY - JOUR

    T1 - Catalytic asymmetric intramolecular cyclopropanation of 2-diazo-3-oxo-6-heptenoic acid esters

    AU - Takeda, Hiroyuki

    AU - Honma, Masahiro

    AU - Ida, Ryoji

    AU - Sawada, Takashi

    AU - Nakada, Masahisa

    PY - 2007/3/1

    Y1 - 2007/3/1

    N2 - This manuscript describes studies on the catalytic asymmetric intramolecular cyclopropanation (IMCP) of 2-diazo-3-oxo-6-heptenoic acid esters. The enantioselectivity depends on the bulkiness of the ester moiety, and the 2,6-di-tert-butyl-4-methylphenyl ester of 2-diazo-3-oxo-6-heptenoic acid provided the product with 78% ee, suggesting that the catalytic asymmetric IMCP of α-diazo-β-keto esters could be a key reaction for the enantioselective synthesis of natural products as well as artificial molecules.

    AB - This manuscript describes studies on the catalytic asymmetric intramolecular cyclopropanation (IMCP) of 2-diazo-3-oxo-6-heptenoic acid esters. The enantioselectivity depends on the bulkiness of the ester moiety, and the 2,6-di-tert-butyl-4-methylphenyl ester of 2-diazo-3-oxo-6-heptenoic acid provided the product with 78% ee, suggesting that the catalytic asymmetric IMCP of α-diazo-β-keto esters could be a key reaction for the enantioselective synthesis of natural products as well as artificial molecules.

    KW - α-diazo-β-keto ester

    KW - Asymmetric catalysis

    KW - Cyclopropanation

    KW - Enantioselectivity

    KW - Intramolecular reaction

    UR - http://www.scopus.com/inward/record.url?scp=33947200459&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=33947200459&partnerID=8YFLogxK

    U2 - 10.1055/s-2007-967964

    DO - 10.1055/s-2007-967964

    M3 - Article

    AN - SCOPUS:33947200459

    SP - 579

    EP - 582

    JO - Synlett

    JF - Synlett

    SN - 0936-5214

    IS - 4

    ER -