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

Naoya Sagawa, Haruka Sato, Seijiro Hosokawa

    Research output: Contribution to journalArticle

    12 Citations (Scopus)

    Abstract

    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.

    Original languageEnglish
    Pages (from-to)198-201
    Number of pages4
    JournalOrganic Letters
    Volume19
    Issue number1
    DOIs
    Publication statusPublished - 2017 Jan 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

    Cite this

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

    In: Organic Letters, Vol. 19, No. 1, 01.01.2017, p. 198-201.

    Research output: Contribution to journalArticle

    Sagawa, Naoya ; Sato, Haruka ; Hosokawa, Seijiro. / Remote asymmetric induction using acetate-type vinylketene silyl N,O-acetals. In: Organic Letters. 2017 ; Vol. 19, No. 1. pp. 198-201.
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