Phosphoramidites:  Marvellous Ligands in Catalytic Asymmetric Conjugate Addition

Ben L. Feringa
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
Acc. Chem. Res., 2000, 33 (6), pp 346–353
DOI: 10.1021/ar990084k
Publication Date (Web): May 31, 2000
Copyright © 2000 American Chemical Society

Ben L. Feringa received his Ph.D. degree from the University of Groningen in 1978 with professor Hans Wynberg. He was a research scientist with Royal Dutch Shell, both at the research center in Amsterdam and at the Shell Biosciences Laboratories at Sittingbourne, UK, from 1978 to 1984. He joined the department of chemistry at the University of Groningen in 1984 as a lecturer and was appointed professor at the same University in 1988. He was visiting professor at the University of Leuven, JSPS fellow, and 1997 recipient of the Pino gold medal of the Italian Chemical Society. With a focus on stereochemistry, his present research interests include organic synthesis, homogeneous (asymmetric) catalysis, molecular switches and motors, self-assembly, and new organic materials.

Abstract

The development of an efficient catalytic system for enantioselective carbon−carbon bond formation by 1,4-addition of organometallic reagents (organolithium, Grignard, and organozinc reagents) to enones is a major challenge in organic synthesis. This Account presents the breakthrough realized in this field using chiral phosphoramidite ligands for copper-catalyzed dialkylzinc additions. Applications in catalytic routes to cycloalkanones as well as tandem and annulation procedures with excellent enantioselectivities are discussed.

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History

  • Published In Issue June 20, 2000
  • Received January 31, 2000

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