Unexpected reversal of stereochemistry observed in the addition of methallyltrimethylsilane to a chiral α-keto imide

Sayaka Ishii, Katsuya Saito, Shigefumi Kuwahara, Masaru Enomoto

    Research output: Contribution to journalArticlepeer-review

    Abstract

    A Lewis acid promoted nucleophilic addition of methallyltrimethylsilane to a chiral a-keto imide proceeded with stereoselectivity opposite to that predicted from Soai's report. The difference in the structure of a-keto imides between Soai's and our cases might have affected the diastereofacial selectivity.

    Original languageEnglish
    Pages (from-to)488-492
    Number of pages5
    JournalBioscience, Biotechnology and Biochemistry
    Volume85
    Issue number3
    DOIs
    Publication statusPublished - 2021 Mar 1

    Keywords

    • reversal of stereochemistry
    • α-hydroxycarboxylic acid
    • α-keto imide

    ASJC Scopus subject areas

    • Biotechnology
    • Analytical Chemistry
    • Biochemistry
    • Applied Microbiology and Biotechnology
    • Molecular Biology
    • Organic Chemistry

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