Diastereodivergent Synthesis of Bromoiminolactones: Electrochemical and Chemical Bromoiminolactonization of α-Allylmalonamides

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<jats:p>A diastereodivergent synthesis of N-substituted iminolactones by bromoiminolactonization of α-substituted α-allylmalonamides is reported. Whereas bromocyclization under conventional chemical conditions provided cis-bromoiminolactones, electrochemical conditions exhibited complementary diastereoselectivity to afford the trans-products. A variety of substituents on the nitrogen atoms and an α-position of the malonamide were tolerated under both sets of conditions to afford the corresponding iminolactones in excellent yields and high diastereoselectivities.</jats:p>

Journal

  • Synlett

    Synlett 30 (10), 1204-1208, 2019-04-18

    Georg Thieme Verlag KG

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