A Coupling Approach for the Generation of α,α-Bis(enolate) Equivalents: Regioselective Synthesis of gem-Difunctionalized Ketones

Carmelo E. Iacono, Thomas C. Stephens, Teena S. Rajan, Graham Pattison

Research output: Contribution to journalArticle

Abstract

Regioselective α,α-difunctionalization adjacent to a ketone is a significant synthetic challenge. Here, we present a solution to this problem through the transition-metal-free coupling of esters with geminal bis(boron) compounds. This forms an α,α-bis(enolate) equivalent which can be trapped with electrophiles including alkyl halides and fluorinating agents. This presents an efficient, convergent synthetic strategy for the synthesis of unsymmetrical blocked ketones.

Original languageEnglish
Pages (from-to)2036-2040
Number of pages5
JournalJournal of the American Chemical Society
Volume140
Issue number6
DOIs
Publication statusPublished - 30 Jan 2018

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