Three-Component Assembly of Multiply Substituted Homoallylic Alcohols and Amines Using a Flow Chemistry Photoreactor

    Yiding Chen , David Blakemore , Patrick Pasau §, Steven V. Ley

    • Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.
    • Medicine Design, Pfizer Inc., Eastern Point Road, Groton, Connecticut 06340, United States
    • § UCB Biopharma SPRL, Chemical Research R5, Chemin du Foriest, 1420 Braine-L’Alleud, Belgium

    Oxadiazolines are bench-stable diazo precursors, which are activated under UV radiation in the presence of vinylboronic acids and aldehydes to enable a one-step three-component assembly of densely functionalized homoallylic alcohols. Substitution on all positions of the homoallylic alcohol product were achieved with high functional group tolerance. No catalyst or other additive was required to effect the reaction, which proceeds at 20 °C over 40 min. Imines and indoles were also incorporated, giving access to homoallylic amines.

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