4.8 Article

Synthesis of γ-Boryl-Substituted Homoallylic Alcohols with anti Stereochemistry Based on a Double-Bond Transposition

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 4, Pages 1138-1142

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201811205

Keywords

allylation; allylic compounds; boron; ruthenium; stereoselective synthesis

Funding

  1. JSPS KAKENHI [15H05756, 16K05694]
  2. JST [ACT-C] [JPMJCR12Z9]
  3. JSPS

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The stereoselective synthesis of anti isomers of gamma-boryl-substituted homoallylic alcohols is disclosed. (E)-1,2-Di(boryl)alk-1-enes undergo Ru-catalyzed double-bond transposition with control of the geometry. The in situ generated (E)-1,2-di(boryl)alk-2-enes add to aldehydes in a stereospecific manner. The alkenylboron group within the product is amenable to a variety of synthetic derivatizations.

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