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

作者：Iacono Carmelo E; Stephens Thomas C; Rajan Teena S; Pattison Graham^*

来源：Journal of the American Chemical Society, 2018, 140(6): 2036-2040.

DOI：10.1021/jacs.7b12941

Regioselective alpha,alpha-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 alpha,alpha-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.

• 出版日期2018-2-14