Pyridinyloxazolidines: versatile scaffolds for chiral catalyst construction.

Pyridinyloxazolidines are structurally versatile chiral ligand frameworks that are easily made and coordinated to Pd(II); the resulting complexes, which show significant steric and electronic differences from their oxazoline counterparts, as well as intermolecular H-bonding in the solid state, can be isolated in diastereomerically pure form and are remarkably resistant to hydrolysis.

[1]  N. D. Jones,et al.  Model intermolecular asymmetric Heck reactions catalyzed by chiral pyridyloxazoline palladium(II) complexes , 2006 .

[2]  L. Wessjohann,et al.  Microwave-accelerated asymmetric allylations using cysteine derived oxazolidine and thiazolidine palladium complexes , 2005 .

[3]  D. S. Lüdtke,et al.  New Simple Chiral Phosphine Oxazolidine Ligands: Easy Synthesis and ­Application in the Palladium-Catalyzed Asymmetric Allylic Alkylation , 2005 .

[4]  Lei Liu,et al.  Enantioselective Alkynylation of Aromatic Ketones Catalyzed by New Chiral Oxazolidine Ligands , 2005 .

[5]  Wenjin Yan,et al.  Enantioselective alkynylation of aromatic aldehydes catalyzed by new chiral oxazolidine ligands , 2005 .

[6]  Gustavo Ríos-Moreno,et al.  Rhodium(I) complexes with phosphinooxathiane (POT) and phophinooxazolidine (POZ) ligands: The crystal structures of [(POT)Rh(CO)Cl] and [(POZ)Rh(CO)Cl] , 2005 .

[7]  Yuichiro Suzuki,et al.  Chiral phosphinooxazolidine ligands for palladium- and platinum-catalyzed asymmetric Diels-Alder reactions. , 2004, The Journal of organic chemistry.

[8]  L. Wessjohann,et al.  First Generation Cysteine‐ and Methionine‐Derived Oxazolidine and Thiazolidine Ligands for Palladium‐Catalyzed Asymmetric Allylations , 2004 .

[9]  F. Couty,et al.  The Use of N‐Boc‐1,3‐Oxazolidines as Chiral Auxiliaries in Asymmetric Synthesis , 2004 .

[10]  Myung-Jong Jin,et al.  Chiral pyridinyloxazolidine ligands for the Pd-catalyzed asymmetric allylic alkylation , 2003 .

[11]  Yuichiro Suzuki,et al.  A novel and efficient chiral palladium–phosphinooxazolidine catalyst for the enantioselective Diels–Alder reactionElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b2/b201625g/ , 2002 .

[12]  Myung-Jong Jin,et al.  Chiral Phosphinooxazolidine Ligand Derived from Prolinol: Application to the Pd-Catalyzed Asymmetric Allylic Alkylation , 2002 .

[13]  A. Pfaltz,et al.  PhosphinooxazolinesA New Class of Versatile, Modular P,N-Ligands for Asymmetric Catalysis , 2000 .

[14]  H. Nakano,et al.  New chiral ligands, pyrrolidinyl- and 2-azanorbornyl- phosphinooxazolidines for palladium-catalyzed asymmetric allylation , 2000 .

[15]  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.

[16]  Myung-Jong Jin,et al.  New chiral phosphinooxazolidine ligands for palladium-catalyzed asymmetric allylic substitution , 1999 .

[17]  Paul-James Jones,et al.  A simple and effective enantiomeric synthesis of a chiral primary amine , 1993 .

[18]  A. Albinati,et al.  Synthesis and molecular structure of optically active oxazolidine complexes of platinum(II) and palladium(II) , 1992 .

[19]  H. Brunner,et al.  Asymmetrische Katalysen, 45. Enantioselektive Hydrosilylierung von Ketonen mit [Rh(COD)Cl]2/Pyridinyloxazolin‐Katalysatoren , 1989 .

[20]  C. Agami,et al.  Stereochemistry-60 : Kinetic control of asymmetric induction during oxazolidine formation from (-)-ephedrine and aromatic aldehydes , 1985 .

[21]  C. Agami,et al.  Role of solvent on the diastereoselectivity of oxazolidine formation from (–)-ephedrine , 1983 .