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Ruthenium-catalyzed formal sp³ C-H activation of allylsilanes/esters with olefins: efficient access to functionalized 1,3-dienes.

ABSTRACT: Ru-catalysed oxidative coupling of allylsilanes and allyl esters with activated olefins has been developed via isomerization followed by C(allyl)-H activation providing efficient access to stereodefined 1,3-dienes in excellent yields. Mild reaction conditions, less expensive catalysts, and excellent regio- and diastereoselectivity ensure universality of the reaction. In addition, the unique power of this reaction was illustrated by performing the Diels-Alder reaction, and enantioselective synthesis of highly functionalized cyclohexenone and piperidine and finally synthetic utility was further demonstrated by the efficient synthesis of norpyrenophorin, an antifungal agent.

SUBMITTER: Dethe DH

PROVIDER: S-EPMC8179449 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Ruthenium-catalyzed formal sp3 C-H activation of allylsilanes/esters with olefins: efficient access to functionalized 1,3-dienes.

Dethe Dattatraya H DH Beeralingappa Nagabhushana C NC Das Saikat S Nirpal Appasaheb K AK

Chemical science 20210202 12

Ru-catalysed oxidative coupling of allylsilanes and allyl esters with activated olefins has been developed via isomerization followed by C(allyl)-H activation providing efficient access to stereodefined 1,3-dienes in excellent yields. Mild reaction conditions, less expensive catalysts, and excellent regio- and diastereoselectivity ensure universality of the reaction. In addition, the unique power of this reaction was illustrated by performing the Diels-Alder reaction, and enantioselective ...[more]

PMID: 34163699

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