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Formation of Boron Enolates by Nucleophilic Substitution

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Enolates have proven to be one of the key building blocks available to the synthetic chemist. Here we summarize a novel strategy for their preparation, involving the addition of α-borylated… Click to show full abstract

Enolates have proven to be one of the key building blocks available to the synthetic chemist. Here we summarize a novel strategy for their preparation, involving the addition of α-borylated nucleophiles to esters to yield boron enolates. The enolates prepared by the addition of lithiated geminal bis(boron) compounds to esters can be trapped with two equivalents of halogen and alkyl electrophiles to yield α,α-difunctionalized compounds. 1 Introduction 2 Ketone Difunctionalization 3 Boron Enolates by Coupling 4 Towards Sequential Trapping 5 Summary and Outlook

Keywords: nucleophilic substitution; enolates nucleophilic; formation boron; boron enolates; boron

Journal Title: Synlett
Year Published: 2020

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