Enantioselective Synthesis of 2-Aryl-4-piperidones via Rhodium/Phosphoramidite-Catalyzed Conjugate Addition of Arylboroxines

Richard B. C. Jagt, Johannes G. de Vries,* Ben L. Feringa,* and Adriaan J. Minnaard*; ;
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
Org. Lett., 2005, 7 (12), pp 2433–2435
DOI: 10.1021/ol050734m
Publication Date (Web): May 17, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, j.g.de.vries@rug.nl, ; , b.l.feringa@rug.nl, ; , a.j.minnaard@rug.nl

Abstract

Abstract Image

The highly enantioselective synthesis of 2-aryl-4-piperidones by rhodium/phosphoramidite-catalyzed conjugate addition of arylboroxines to 2,3-dihydro-4-pyridones is described. Both enantiomers of a variety of products with sterically and electronically different R substituents were obtained in high isolated yield and with excellent enantioselectivity up to 99%.

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History

  • Published In Issue June 09, 2005
  • Received April 6, 2005

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