首页|Stereospecific Assembly of Trisubstituted Alkenes via Photoinduced Nitrogen-Centered Radical-Triggered C-C Bond Cleavage/Functionalization of Oxime Esters
Stereospecific Assembly of Trisubstituted Alkenes via Photoinduced Nitrogen-Centered Radical-Triggered C-C Bond Cleavage/Functionalization of Oxime Esters
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A general and convenient photoredox-catalyzed acylation and alkylcyanation of MBH acetates has been established,enabling the as-sembly of the C(sp2)-C(sp3)bond by a nitrogen-centered radical strategy for the synthesis of trisubstituted alkenes in moderate to excellent chemical yields(48 examples in total).The reaction of MBH acetates with acyl(indanone)oxime esters afforded trisubsti-tuted alkenes containing 1,4-dicarbonyl groups.Interestingly,the use of Eosin Y as a photocatalyst in the catalytic system resulted in the formation of distal cyano group-anchored trisubstituted alkenes via deconstructive functionalization of cycloketone oxime esters.Notably,these resulting 1,4-dicarbonyl compounds could be applied to late-stage transformations,providing important methods for the synthesis of dihydropyridazin-3(2H)-one.
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