Base-Catalyzed Isomerization of 2-Isoxazolines Enables a Two-Step Enantioselective Synthesis of beta-Hydroxynitriles from Enals

Antti Pohjakallio, Petri M. Pihko*, Jun Liu

*Corresponding author for this work

    Research output: Contribution to journalArticleScientificpeer-review

    Abstract

    The asymmetric synthesis of beta-hydroxynitriles remains a challenge in organic synthesis. Herein we report a convenient synthesis of beta-hydroxynitriles from enantiomerically enriched 3-unsubstituted 2-isoxazolines via a base-catalyzed ring-opening reaction that takes place without loss of enantiopurity. In combination with organocatalytic enantioselective synthesis of 3-unsubstituted 2-isoxazolines, the ring-opening enables a short 2-step synthesis of beta-hydroxynitriles from alpha,beta-unsaturated aldehydes in high enantiomeric purity.

    Original languageEnglish
    Pages (from-to)6712-6715
    Number of pages4
    JournalJournal of organic chemistry
    Volume75
    Issue number19
    DOIs
    Publication statusPublished - 1 Oct 2010
    MoE publication typeA1 Journal article-refereed

    Keywords

    • ASYMMETRIC TRANSFER HYDROGENATION
    • RU-TSDPEN CATALYSTS
    • HYDROXY NITRILES
    • ORGANIC-SYNTHESIS
    • LIPASE
    • RESOLUTION
    • ALDEHYDES
    • KETONES
    • ACETONITRILE
    • ISOXAZOLINES

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