Iacano, Carmelo E., Stephens, Thomas C., Rajan, Teena S. et al 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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Item Type: | Article |
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Item Status: | Live Archive |
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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.
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