A rare example of the umpolung of an enolate forms the basis of the title reaction. In this procedure, a Grignard reagent is added to the iminium ion formed from the Weinreb amide upon treatment with a base (see scheme). When a chiral amide was used as the starting material, the nucleophilic addition proceeded with high diastereoselectivity. LDA = lithium diisopropylamide.
Wenige Beispiele für die Umpolung von Enolaten sind bekannt, doch ein solcher Prozess liegt der Titelreaktion zugrunde: Aus einem Weinreb‐Amid wird durch Umsetzung mit einer Base zunächst ein Iminiumion gebildet, an das anschließend ein Grignard‐Reagens addieren kann (siehe Schema). Chirale Amide führten zu hoch diastereoselektiven nucleophilen Additionen. LDA = Lithiumdiisopropylamid.
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