Catalytic, nucleophilic allylation of aldehydes with 2-substituted allylic acetates: Carbon-carbon bond formation driven by the water-gas shift reaction

Scott E Denmark, Zachery D. Matesich

Research output: Contribution to journalArticle

Abstract

The ruthenium-catalyzed allylation of aldehydes with allylic acetates has been expanded to incorporate substituents at the 2-position of the allylic components. Allylic acetates bearing a variety of substituents (CO 2 -t-Bu, COMe, Ph, CH(OEt) 2 , and Me) undergo high-yielding additions with aromatic, α,β-unsaturated, and aliphatic aldehydes. The conditions of the reaction were found to be mild (75°C, 24-48 h) and only required the use of 2-3 mol % of the triruthenium dodecacarbonyl catalyst under 40-80 psi of CO. The stoichiometries of water and allylic acetate employed were found to be critical to reaction efficiency.

Original languageEnglish (US)
Pages (from-to)5970-5986
Number of pages17
JournalJournal of Organic Chemistry
Volume79
Issue number13
DOIs
StatePublished - Jul 3 2014

ASJC Scopus subject areas

  • Organic Chemistry

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