Synlett 2020; 31(17): 1656-1662
DOI: 10.1055/s-0040-1707181
synpacts
© Georg Thieme Verlag Stuttgart · New York

Formation of Boron Enolates by Nucleophilic Substitution

George R. A. Garratt
,
We thank the University of Brighton for support and funding.
Further Information

Publication History

Received: 14 May 2020

Accepted after revision: 30 May 2020

Publication Date:
09 July 2020 (online)


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

 
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