Palladium-catalyzed asymmetric allylic alkylation of meso- and dl-1,2-divinylethylene carbonate.

The palladium-catalyzed asymmetric allylic alkylation of a 1:1 mixture of dl- and meso-1,2-divinylethylene carbonate is reported. For the first time, both the ionization and nucleophilic addition steps of the catalytic cycle act as enantiodiscriminating steps to give a single product in high enantiomeric excess. The reactions proceed in >98% ee to efficiently generate useful chiral building blocks from acrolein. The absolute and relative configurations of iso-cladospolide B and 11-epi-iso-cladospolide B were verified by total synthesis, solving an apparent discrepancy in the literature.

• Publication year

  2006

• Venue

  Journal of the American Chemical Society

• Publication date

  2006-03-29

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/JA0578348PMID 16551099PMCID PMC2531165
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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