The development and application of chiral trisoxazolines in asymmetric catalysis and molecular recognition.

The development of suitable ligands that upon coordination to a metal facilitate enantioselective reactions or are able to selectively recognize a molecule are fundamental endeavours in organic chemistry. Chiral ligands that contain one or two oxazoline groups have been extensively studied and applied successfully to many metal catalyzed reactions. Accordingly, the development and application of chiral trisoxazolines has received increasing attention in the last decade. This tutorial review covers the synthetic methods for the preparation of chiral trisoxazolines, the application of chiral trisoxazolines in asymmetric catalysis and molecular recognition.

[1]  Benjamin D. Ward,et al.  C3 chirality in polymerization catalysis: a highly active dicationic scandium(III) catalyst for the isoselective polymerization of 1-hexene. , 2005, Angewandte Chemie.

[2]  K. Ahn,et al.  Synthesis of C1-symmetric chiral tripodal oxazolines through an oxazoline exchange reaction with amino alcohols , 2004 .

[3]  S. Bellemin‐Laponnaz,et al.  A C3-symmetrical chiral trisoxazoline zinc complex as a functional model for zinc hydrolases: kinetic resolution of racemic chiral esters by transesterification. , 2004, Angewandte Chemie.

[4]  P. Guiry,et al.  Recent developments in the application of oxazoline-containing ligands in asymmetric catalysis. , 2004, Chemical reviews.

[5]  Jian Zhou,et al.  Diastereoselectivity-switchable and highly enantioselective 1,3-dipolar cycloaddition of nitrones to alkylidene malonates. , 2004, Organic letters.

[6]  Jian Zhou,et al.  Sidearm approach: a promising strategy for construction of bisoxazoline-based ligand library. , 2004, Journal of combinatorial chemistry.

[7]  Jian Zhou,et al.  Enantioselective Friedel-Crafts reaction of indoles with arylidene malonates catalyzed by iPr-bisoxazoline-Cu(OTf)2. , 2004, Chemical communications.

[8]  Jian Zhou,et al.  Pseudo-C3-symmetric trisoxazolines as ligands in copper catalyzed enantioselective Diels-Alder reaction. , 2004, Organic & biomolecular chemistry.

[9]  Jian Zhou,et al.  Controllable enantioselective Friedel-Crafts reaction between indoles and alkylidene malonates catalyzed by pseudo-C3-symmetric trisoxazoline copperII complexes. , 2004, The Journal of organic chemistry.

[10]  K. Ahn,et al.  Crucial role of three-center hydrogen bonding in a challenging chiral molecular recognition. , 2003, Journal of the American Chemical Society.

[11]  Jian Zhou,et al.  Chiral tris(oxazoline)/Cu(II) catalyzed coupling of terminal alkynes and nitrones. , 2003, Chemical communications.

[12]  M. Franzini,et al.  Toggling enantioselective catalysis--a promising paradigm in the development of more efficient and versatile enantioselective synthetic methodologies. , 2003, Chemical Society reviews.

[13]  K. Ahn,et al.  Fluorescence sensing of ammonium and organoammonium ions with tripodal oxazoline receptors. , 2003, Organic letters.

[14]  V. Fino,et al.  Michael addition of chloroalkyloxazolines to electron-poor alkenes: synthesis of heterosubstituted cyclopropanes. , 2003, The Journal of organic chemistry.

[15]  S. Bellemin‐Laponnaz,et al.  A modular approach to C1 and C3 chiral N-tripodal ligands for asymmetric catalysis. , 2002, Angewandte Chemie.

[16]  Jian Zhou,et al.  Sidearm effect: improvement of the enantiomeric excess in the asymmetric Michael addition of indoles to alkylidene malonates. , 2002, Journal of the American Chemical Society.

[17]  K. Ahn,et al.  Unprecedented chiral molecular recognition in a C3-symmetric environment. , 2002, Journal of the American Chemical Society.

[18]  Jong‐In Hong,et al.  Sugar recognition by C 3 -symmetric oxazoline hosts , 2001 .

[19]  K. Ahn,et al.  Enantioselective Michael addition catalyzed by chiral tripodal oxazoline–tBuOK complexes , 2001 .

[20]  Fr'ed'eric Naud,et al.  Hemilability of Hybrid Ligands and the Coordination Chemistry of Oxazoline-Based Systems. , 2001, Angewandte Chemie.

[21]  W. Zhuang,et al.  Catalytic enantioselective alkylation of heteroaromatic compounds using alkylidene malonates , 2001 .

[22]  K. Kawasaki,et al.  BENZYLIC AND ALLYLIC AMINATION , 2000 .

[23]  Ahn,et al.  Novel artificial receptors for alkylammonium ions with remarkable selectivity and affinity , 2000, Chemistry.

[24]  T. Katsuki,et al.  Asymmetric allylic oxidation of cycloalkenes using a tridentate tris(oxazoline) ligand as a chiral auxiliary , 2000 .

[25]  M. Lemaire,et al.  Nitrogen-containing ligands for asymmetric homogeneous and heterogeneous catalysis. , 2000, Chemical reviews.

[26]  C. Bolm,et al.  Preparation and Catalytic Enantioselective Reactions of C 3-Symmetric Tris(Oxazoline)s Derived from Kemp's Triacid , 2000 .

[27]  C. Baldino.  Perspective Articles on the utility and application of solution-phase combinatorial chemistry. , 2000, Journal of combinatorial chemistry.

[28]  Kimoon Kim,et al.  Selective Recognition of NH4+ over K+ with Tripodal Oxazoline Receptors , 2000 .

[29]  J. S. Johnson,et al.  Chiral bis(oxazoline) copper(II) complexes: versatile catalysts for enantioselective cycloaddition, Aldol, Michael, and carbonyl ene reactions. , 2000, Accounts of chemical research.

[30]  T. Katsuki,et al.  Oxidative Asymmetrization of Racemic Alkenes: Asymmetric Synthesis of Optically Active Dicyclopentadiene Derivatives , 1999 .

[31]  H. Audrain,et al.  Catalytic Asymmetric Addition Reactions of Carbonyls. A Common Catalytic Approach , 1999 .

[32]  C. Moberg.  C3 Symmetry in Asymmetric Catalysis and Chiral Recognition. , 1998, Angewandte Chemie.

[33]  Arun K. Ghosh,et al.  C 2-Symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis. , 1998, Tetrahedron, asymmetry.

[34]  T. Chan,et al.  C3 Symmetric oxazolinyl ligand as catalyst in the enantioselective addition of diethylzinc to aldehydes , 1997 .

[35]  K. Kawasaki,et al.  Enantioselective allylic oxidation of cycloalkenes by using Cu(II)-tris(oxazoline) complex as a catalyst , 1997 .

[36]  K. Kawasaki,et al.  ENANTIOSELECTIVE ALLYLIC OXIDATION USING BIOMIMETIC TRIS(OXAZOLINES)-COPPER(II) COMPLEX , 1995 .

[37]  P. White,et al.  Synthesis and structural characterization of a Cu(I) dimer of a tris(oxazoline) ligand , 1993 .

[38]  K. Herzfeld,et al.  Die chemische Valenz als Energiefrage , 1924 .