Palladium-Catalyzed Carbonylative Couplings of Vinylogous Enolates: Application to Statin Structures

Ilya S. Makarov, Takashi Kuwahara, Xavier Jusseau, Ilhyong Ryu, Anders T. Lindhardt*, Troels Skrydstrup

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

The first Pd-catalyzed carbonylative couplings of aryl and vinyl halides with vinylogous enolates are reported generating products derived from C-C bond formation exclusively at the γ-position. Good results were obtained with a dienolate derivative of acetoacetate (1,3-dioxin-4-one). These transformations occurred at room temperature and importantly with only stoichiometric carbon monoxide in a two-chamber reactor. The methodology was applied to the synthesis of two members of the statin family generating the cis-3,5-diol acid motif by a γ-selective carbonylation followed by a cis-stereoselective reduction of the 3,5-dicarbonyl acid intermediates.

Original languageEnglish
Pages (from-to)14043-14046
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number44
DOIs
StatePublished - 11 Nov 2015

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