Formation of Boron Enolates by Nucleophilic Substitution

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

Key words

enolates - coupling - boron - fluorination

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