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Lops, Carmine; Pengo, Paolo; Pasquato, Lucia
ChemistryOpen (Weinheim), October 2022, 2022-10-00, 20221001, 2022-10-01, Volume: 11, Issue: 10Journal Article
The highly basic and poorly nucleophilic phosphazene base P1‐t‐Bu promotes the Darzens condensation of α‐halo esters with aromatic aldehydes affording α,β‐epoxy esters in nearly quantitative yields under mild conditions and in short reaction times. The more basic P4‐t‐Bu phosphazene was found useful with low reactivity aldehydes. These reactions can be performed in aprotic organic solvents of low polarity, thus minimizing the hydrolysis of α,β‐epoxy esters which often accompanies the base‐promoted Darzens condensations. The first Darzens reaction of α‐halo acetate esters with aromatic aldehydes promoted by phosphazene bases is reported. The reactions proceed smoothly, affording α,β‐epoxy esters in nearly quantitative yields, short time, and no side products. The phosphazene base P1‐t‐Bu can be used with aldehydes carrying electron‐withdrawing groups, while the base P4‐t‐Bu is preferable when the aldehydes carry electron donating substituents.
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