e-space
Manchester Metropolitan University's Research Repository

    Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines vial-phenylalanine-derived dihydroisoquinoline N-oxides

    Flores-Ferrándiz, Jesús, Carter, Nicholas, González-Soria, Maria José, Wasinska, Malgorzata, Gill, Daniel, Maciá, Beatriz and Caprio, Vittorio (2018) Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines vial-phenylalanine-derived dihydroisoquinoline N-oxides. Organic and Biomolecular Chemistry, 16 (38). pp. 6961-6968. ISSN 1477-0539

    [img]
    Preview
    Published Version
    Available under License Creative Commons Attribution.

    Download (350kB) | Preview

    Abstract

    The preparation of chiral pool-derived nitrone 3 and its use in the protecting-group free, stereoselective synthesis of a range of 1,3-disubstituted tetrahydroisoquinolines is described. Grignard reagent additions to nitrone 3 yielded trans-1,3-disubstituted N-hydroxytetrahydroisoquinolines 6 with good levels of selectivity, while 1,3-dipolar cycloadditions to this nitrone provided access to 3-(2-hydroxyalkyl)isoquinolines 12 as single diastereomers.

    Impact and Reach

    Statistics

    Activity Overview
    6 month trend
    351Downloads
    6 month trend
    381Hits

    Additional statistics for this dataset are available via IRStats2.

    Altmetric

    Repository staff only

    Edit record Edit record