Electroreductive intramolecular coupling of γ- and δ-cyanoketones☆
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Cited by (40)
A simple one-pot oxidation protocol for the synthesis of dehydrohedione from Hedione
2022, TetrahedronCitation Excerpt :Enhanced cis isomer mixtures possess a superior scent profile and hence are worth more than commercial Hedione (90% trans). Although a wide variety of synthetic routes towards DHH have been developed [7–13], Hedione is cheap (∼$5/kg) and readily available in its predominantly trans form (1c + 1d) and so the preferred method of DHH synthesis at scale is through direct oxidation of Hedione [14]. Historically, this has been enacted via a 3 steps sequence involving regioselective formation of ester 3, followed by bromination with a bromine source (typically Br2), followed by base induced elimination.
Nitriles as radical acceptors in radical cascade reactions
2021, Organic Chemistry Frontiersα,β-Unsaturated ketones via copper(II) bromide mediated oxidation
2016, TetrahedronCitation Excerpt :This is primarily achieved through hydrogenation of DHH (1b, its α,β-unsaturated analogue). Although several novel syntheses of DHH have been developed,15–20 the preferred method of DHH synthesis at scale still remains the direct oxidation of Hedione®.21 Herein, we report a convenient and operationally simple means of effecting the oxidative transformation of enol acetates to α,β-unsaturated ketones in a single step using superstoichiometric amounts of copper(II) bromide.
Acyloin Coupling Reactions
2014, Comprehensive Organic Synthesis: Second Edition
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Electroorganic Chemistry. 123.