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

Iacano, Carmelo E., Stephens, Thomas C., Rajan, Teena S. and Pattison, Graham (2018) A Coupling Approach for the Generation of α,α-Bis(enolate) Equivalents: Regioselective Synthesis of gem-Difunctionalized Ketones. Journal of the American Chemical Society, 140 (6). pp. 2036-2040. ISSN 0002-7863

Full content URL: https://doi.org/10.1021/jacs.7b12941

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

Keywords:fluorination, Ketones, Boron, selectivity
Subjects:F Physical Sciences > F100 Chemistry
Divisions:College of Science > School of Chemistry
ID Code:52242
Deposited On:31 Oct 2022 14:46

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