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α-Vinylation of Ester Equivalents via Main Group Catalysis for the Construction of Quaternary Centers.

ABSTRACT: A methodology for the construction of sterically congested quaternary centers via the trapping of vinyl carbocations with silyl ketene acetals is disclosed. This main group-catalyzed α-vinylation reaction is advantageous as methods to access these congested motifs are limited. Moreover, β,γ-unsaturated carbonyl moieties and tetrasubstituted alkenes are present in various bioactive natural products and pharmaceuticals, and this catalytic platform offers a means of accessing them using simple and inexpensive materials.

SUBMITTER: Williams CG

PROVIDER: S-EPMC10226172 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature

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α-Vinylation of Ester Equivalents via Main Group Catalysis for the Construction of Quaternary Centers.

Williams Chloe G CG Nistanaki Sepand K SK Wells Conner W CW Nelson Hosea M HM

Organic letters 20230516 20

A methodology for the construction of sterically congested quaternary centers via the trapping of vinyl carbocations with silyl ketene acetals is disclosed. This main group-catalyzed α-vinylation reaction is advantageous as methods to access these congested motifs are limited. Moreover, β,γ-unsaturated carbonyl moieties and tetrasubstituted alkenes are present in various bioactive natural products and pharmaceuticals, and this catalytic platform offers a means of accessing them using simple and ...[more]

PMID: 37192420

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