4.8 Article

Ruthenium-Catalyzed Enantioselective Propargylic Phosphinylation of Propargylic Alcohols with Phosphine Oxides

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 20, Pages 11231-11236

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202102779

Keywords

DFT calculations; enantioselective reactions; propargylic phosphinylation; propargylic substitution reaction; ruthenium

Funding

  1. CREST, JST [JPMJCR1541]
  2. JSPS [20H05671, 20K21203]
  3. MEXT
  4. JSPS

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In recent years, significant progress has been made in the development of transition metal-catalyzed enantioselective propargylic substitution reactions. However, until now, no successful example with phosphorus-centered nucleophiles has been reported. This study presents the first successful example of ruthenium-catalyzed enantioselective propargylic substitution reactions using propargylic alcohols as substrates and diarylphosphine oxides as phosphorus-centered nucleophiles, providing a new method for preparing chiral phosphorus-containing organic compounds.
The development of transition metal-catalyzed enantioselective propargylic substitution reactions has gained much progress in recent years, however, no successful example with phosphorus-centered nucleophiles has yet been reported until now. Herein, we report the first successful example of ruthenium-catalyzed enantioselective propargylic substitution reactions of propargylic alcohols with diarylphosphine oxides as phosphorus-centered nucleophiles. This synthetic approach provides a new method to prepare chiral phosphorus-containing organic compounds.

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