Enantioselective Mukaiyama-Michael Reaction of Cyclic α-Alkylidene β-Keto Phosphine Oxide and Phosphonate and Asymmetric Synthesis of (R)-Homosarkomycin

Kotaro Nagatani, Atsushi Minami, Haruka Tezuka, Yunosuke Hoshino, Masahisa Nakada

    Research output: Contribution to journalArticle

    9 Citations (Scopus)

    Abstract

    The asymmetric Mukaiyama-Michael reaction of cyclic α-alkylidene β-oxo phosphates and phosphine oxides that proceeds in a highly enantioselective manner is described. It is possible to carry out these reactions using a catalytic amount of a bisoxazoline-Cu(II) complex without decreasing the enantioselectivity, and one of the products has been successfully used for the first enantioselective synthesis of (R)-homosarkomycin.

    Original languageEnglish
    Pages (from-to)810-813
    Number of pages4
    JournalOrganic Letters
    Volume19
    Issue number4
    DOIs
    Publication statusPublished - 2017 Feb 17

    Fingerprint

    phosphine
    Michael reaction
    alkylidene
    Organophosphonates
    Enantioselectivity
    phosphines
    Oxides
    phosphates
    Phosphates
    oxides
    synthesis
    products
    homosarkomycin

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

    Cite this

    Enantioselective Mukaiyama-Michael Reaction of Cyclic α-Alkylidene β-Keto Phosphine Oxide and Phosphonate and Asymmetric Synthesis of (R)-Homosarkomycin. / Nagatani, Kotaro; Minami, Atsushi; Tezuka, Haruka; Hoshino, Yunosuke; Nakada, Masahisa.

    In: Organic Letters, Vol. 19, No. 4, 17.02.2017, p. 810-813.

    Research output: Contribution to journalArticle

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    AU - Minami, Atsushi

    AU - Tezuka, Haruka

    AU - Hoshino, Yunosuke

    AU - Nakada, Masahisa

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