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• W4321253643 abstract "Dienones are challenging building blocks in natural product synthesis due to their high reactivity and complex synthesis. Based on previous work and own initial results, a new stereospecific sequential hydrozirconation/Pd-catalyzed acylation of enynes with acyl chlorides towards conjugated (2 E ,4 E )-dienones is reported. We investigated a number of substrates with different alkyl and aryl substituents in the one-pot reaction and showed that regardless of the substitution pattern, the reactions lead to the stereoselective formation (≥95% (2 E ,4 E )) of the respective dienones under mild conditions. It was found that enynes with alkyl chains gave higher yields than the corresponding aryl-substituted analogues, whereas the variation of the acyl chlorides did not affect the reaction significantly. The synthetic application is demonstrated by formation of non-natural and natural dienone-containing terpenes such as β-ionone which was available in 4 steps and 6% overall yield." @default.
• W4321253643 created "2023-02-18" @default.
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• W4321253643 date "2023-02-17" @default.
• W4321253643 modified "2023-10-14" @default.
• W4321253643 title "Sequential hydrozirconation/Pd-catalyzed cross coupling of acyl chlorides towards conjugated (2<i>E</i>,4<i>E</i>)-dienones" @default.
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• W4321253643 doi "https://doi.org/10.3762/bjoc.19.17" @default.
• W4321253643 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/36814450" @default.
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