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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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Iacono, 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. doi:10.1021/jacs.7b12941 ISSN 0002-7863.
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Official URL: http://dx.doi.org/10.1021/jacs.7b12941
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.
Item Type: | Journal Article | |||||||||
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Subjects: | Q Science > QD Chemistry | |||||||||
Divisions: | Other > Institute of Advanced Study Faculty of Science, Engineering and Medicine > Science > Chemistry |
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Library of Congress Subject Headings (LCSH): | Ketones -- Synthesis, Enols, Carbonyl compounds | |||||||||
Journal or Publication Title: | Journal of the American Chemical Society | |||||||||
Publisher: | American Chemical Society | |||||||||
ISSN: | 0002-7863 | |||||||||
Official Date: | 30 January 2018 | |||||||||
Dates: |
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Volume: | 140 | |||||||||
Number: | 6 | |||||||||
Page Range: | pp. 2036-2040 | |||||||||
DOI: | 10.1021/jacs.7b12941 | |||||||||
Status: | Peer Reviewed | |||||||||
Publication Status: | Published | |||||||||
Access rights to Published version: | Restricted or Subscription Access | |||||||||
Date of first compliant deposit: | 10 April 2018 | |||||||||
Date of first compliant Open Access: | 30 January 2019 | |||||||||
RIOXX Funder/Project Grant: |
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