4.7 Article

A Diastereoselective One-Pot, Three-Step Cascade toward α-Substituted Allylboronic Esters

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 10, Pages 4699-4703

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo5004168

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Funding

  1. Fonds der Chemischen Industrie
  2. Deutsche Forschungsgemeinschaft
  3. Heinrich-Heine-Universitat Dusseldorf
  4. Forschungszentrum Julich GmbH

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A new highly diastereoselective synthesis of chiral a-substituted allylboronic esters, based on a one-pot, three-step cascade, is presented. The palladium- and acid-cocatalyzed reaction cascade involves a desilylation of a TBS-protected allylic alcohol, borylation, and addition of an allyl group to an aldehyde. Herein we present the first application of a TBS-protected allylic alcohol in a palladium-catalyzed borylation/allylation reaction.

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