Going for Gold in Chiral Amine Synthesis

  • ChemPubSoc Europe Logo
  • Author: Lois O'Leary
  • Published Date: 18 August 2014
  • Source / Publisher: ChemCatChem/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Going for Gold in Chiral Amine Synthesis

Related Societies

Amines are synthesized most effectively by hydroamination of unactivated alkenes, the enantioselective version of which is best achieved by metal catalysis. Binuclear gold(I) caomplexes can catalyze the hydroamination of alkenes, however, the harsh and stringent reactions conditions required have prevented full development of this metal for synthesis of chiral amines. In addition, the exact catalytic species involved and whether the activating silver salt participates haChiral Amine Synthesiss remained a mystery. 


Christophe Michon, Francine Agbossou-Niedercorn and co-workers, Université Lille Nord de France, have shown that a diphosphine binuclear gold(I) chloride complex catalyzes alkene hydroamination under mild conditions with water as the solvent. Silver perchlorate is used to activate the gold center. Their system shows conversions of up to 97 % and good enantioselectivities. They have also solved the mystery of the catalytic gold species, proving that no silver is involved in the catalysis step by solid state X-ray analysis and diffusion-ordered 1H-NMR spectroscopy. This proved the role of the silver salt was in activating the gold and not in the catalysis.

The group also demonstrated a solvent polarity switch for controlling the molecular ion pairs in the catalyst and, subsequently, the chirality of the product. 


 

Article Views: 2377

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH