Remote asymmetric induction using acetate-type vinylketene silyl N,O-acetals

Naoya Sagawa, Haruka Sato, Seijiro Hosokawa

    研究成果: Article

    12 引用 (Scopus)

    抄録

    Remote asymmetric induction by the vinylogous Mukaiyama aldol reaction using the acetate-type vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved. The silyl N,O-acetal derived from crotonate and L-valine afforded the O-silylated 5R- and 5S-adducts selectively by treatment with SnCl4 and BF3·OEt2, respectively. The SnCl4-mediated isomerization of silyl dienol ether was found, and the resulting major isomer showed high reactivity to give γ-adduct in high stereoselectivity.

    元の言語English
    ページ(範囲)198-201
    ページ数4
    ジャーナルOrganic Letters
    19
    発行部数1
    DOI
    出版物ステータスPublished - 2017 1 1

    Fingerprint

    acetals
    Acetals
    adducts
    acetates
    induction
    Acetates
    Crotonates
    Stereoselectivity
    Valine
    Isomerization
    Isomers
    Ether
    isomerization
    ethers
    isomers
    reactivity
    stannic chloride
    3-hydroxybutanal

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

    これを引用

    Remote asymmetric induction using acetate-type vinylketene silyl N,O-acetals. / Sagawa, Naoya; Sato, Haruka; Hosokawa, Seijiro.

    :: Organic Letters, 巻 19, 番号 1, 01.01.2017, p. 198-201.

    研究成果: Article

    Sagawa, Naoya ; Sato, Haruka ; Hosokawa, Seijiro. / Remote asymmetric induction using acetate-type vinylketene silyl N,O-acetals. :: Organic Letters. 2017 ; 巻 19, 番号 1. pp. 198-201.
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