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Palladium-catalysed 5-endo-trig allylic (hetero)arylation.

ABSTRACT: A palladium-catalysed intramolecular allylic (hetero)arylation strategy for the synthesis of fused cyclopentenes incorporated with all-carbon quaternary and spiro centres is described. The method is straightforward, shows broad scope, proceeds in synthetically useful yields, and provides a rare means to construct complex cyclopentanoids. The reaction is believed to involve a kinetically unfavourable 5-endo-trig carbocyclisation of the tethered (π-allyl)palladium system. Further, this method was successfully applied as the key step in the total synthesis of diterpene natural products taiwaniaquinone H and dichroanone.

SUBMITTER: Singh B

PROVIDER: S-EPMC8159216 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Palladium-catalysed 5-<i>endo-trig</i> allylic (hetero)arylation.

Singh Bara B Bankar Siddheshwar K SK Kumar Ketan K Ramasastry S S V SSV

Chemical science 20200430 19

A palladium-catalysed intramolecular allylic (hetero)arylation strategy for the synthesis of fused cyclopentenes incorporated with all-carbon quaternary and spiro centres is described. The method is straightforward, shows broad scope, proceeds in synthetically useful yields, and provides a rare means to construct complex cyclopentanoids. The reaction is believed to involve a kinetically unfavourable 5-<i>endo-trig</i> carbocyclisation of the tethered (π-allyl)palladium system. Further, this meth ...[more]

PMID: 34122951

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