文档介绍:Chem. Rev. 2004, 104, 4151−4202 4151
Recent Developments in the Application of Oxazoline-Containing Ligands in
Asymmetric Catalysis
Helen A. McManus and Patrick J. Guiry*
Centre for Synthesis and Chemical Biology, Conway Institute of Biomolecular and Biomedical Research, Department of Chemistry,
University College Dublin, Belfield, Dublin 4, Ireland
Received March 8, 2004
Contents essful, versatile, monly used classes of
ligands for asymmetric -3 The large major-
1. Introduction 4151 ity of these ligands are derived from readily available
2. Bidentate Mono(oxazoline) Ligands 4151 chiral amino alcohols in a few high-yielding synthetic
. Mono(oxazoline) P,N-Ligands 4151 steps. As a consequence, the enantiocontrolling ste-
. Phosphinooxazoline Ligands with Only a 4151 reocenter resides on the carbon atom neighboring the
Stereocenter coordinating nitrogen of the oxazoline ring and,
. Phosphinooxazoline Ligands with a 4158 therefore, in close proximity to the metal active site,
Stereoaxis thus having a direct influence on the stereochemical
. Phosphinooxazoline Ligands with a 4160 e of the reaction.
Stereoplane Since the first report in 1986 of the use of chiral
. Oxazoline−Phosphinite Ligands 4164 oxazoline-based ligands in asymmetric catalysis,4 a
. Oxazoline Ligands with Phosphorus 4165 diverse range of ligands with one, two, or more
Bonded to One N Atom oxazoline rings incorporating various heteroatoms,
. Oxazoline−Phosphonamidate Ligands 4166 additional chiral elements, and specific structural
. Oxazoline−Phosphoramidate Ligands 4167 features have been used with great ess in a wide
. Oxazoline−Phosphite Ligands 4167 range of asymmetric reactions. The aim of this review
. Mono(oxazoline) N,N-Ligands 4169 is to report the use of such ligands in homogeneous
. Mono(oxazoline) N,O-Ligands 4174 metal-catalyzed asymmetric synthesis, concentrating
in particular on