The first series of chiral 2,2':6',2''-terpyridine tri-N-oxide ligands for Lewis base-catalyzed asymmetric allylation of aldehydes.

The first series of chiral 2,2':6',2''-terpyridine tri-N-oxide ligands have been developed; They were showed to be active Lewis base-catalysts for asymmetric allylation of aldehydes using allyltrichlorosilane with optimal results at 0 degrees C for electron-deficient aromatic aldehydes (yields up to 97% and enantioselectivities up to 86% ee).

[1]  A. Yudin,et al.  Modified BINOL ligands in asymmetric catalysis. , 2003, Chemical reviews.

[2]  P. Kočovský,et al.  Quinox, a quinoline-type N-oxide, as organocatalyst in the asymmetric allylation of aromatic aldehydes with allyltrichlorosilanes: the role of arene-arene interactions. , 2003, Angewandte Chemie.

[3]  T. Shimada,et al.  A novel axially chiral 2,2'-bipyridine N,N'-dioxide. Its preparation and use for asymmetric allylation of aldehydes with allyl(trichloro)silane as a highly efficient catalyst. , 2002, Organic letters.

[4]  T. Gelbrich,et al.  The oxidation and subsequent co-ordination chemistries of 4′,4″-diphenyl-2,2′:6′,2″:6″,2‴-quaterpyridine , 2002 .

[5]  H. C. Aspinall.  Chiral lanthanide complexes: coordination chemistry and applications. , 2002, Chemical reviews.

[6]  S. Denmark,et al.  Catalytic, enantioselective aldol additions to ketones. , 2002, Journal of the American Chemical Society.

[7]  V. Langer,et al.  Chiral 2,2'-bipyridine-type N-monoxides as organocatalysts in the enantioselective allylation of aldehydes with allyltrichlorosilane. , 2002, Organic letters.

[8]  G. C. Fu,et al.  Planar-chiral pyridine N-oxides, a new family of asymmetric catalysts: exploiting an eta(5)-C(5)Ar(5) ligand to achieve high enantioselectivity. , 2001, Journal of the American Chemical Society.

[9]  W. Wong,et al.  Geometrical preferences of complexes of terpyridine N-oxide ligands: synthesis and crystal structures of nickel(II) with terpyridine 1,1′,1″-trioxide, terpyridine 1,1″-dioxide and terpyridine 1-oxide , 2001 .

[10]  S. Hashimoto,et al.  Enantioselective Michael addition of beta-keto esters to methyl vinyl ketone employing a chiral N,N'-dioxide-scandium trifluoromethanesulfonate complex as a catalyst. , 2001, Chemical communications.

[11]  Martina Vrbová,et al.  Preparation and structure of 2-(2-benzimidazol-2-yl)pyridine N-oxide and its complexes , 2000 .

[12]  H. Doucet,et al.  Titanium catalysed enantioselective addition of allyltributyltin to aldehydes: a simple and easily reproducible procedure , 2000 .

[13]  R. Boča,et al.  Zinc(II) trinuclear complexes involving pyridine N-oxide ligands: distortion isomerism and magnetic properties of copper(II) analogues , 2000 .

[14]  H. Kwong,et al.  First enantioselective catalyst based on a chiral terpyridine: synthesis of new C2-symmetric 2,2′:6′,2′′-terpyridine ligands and copper-catalyzed enantioselective cyclopropanation of alkenes , 2000 .

[15]  S. Hashimoto,et al.  Enantioselective conjugate addition of thiols to enones and enals catalyzed by chiral N-oxide–cadmium complex , 2000 .

[16]  G. Henkel,et al.  A chiral bis-N-oxide isoelectronic with Jacobsen's salen ligand , 1999 .

[17]  H. Kwong,et al.  Chiral zinc(II) bipyridine complex. Crystal structure and catalytic activity in asymmetric allylation reaction , 1999 .

[18]  M. Shiro,et al.  (S)-3,3‘-Dimethyl-2,2‘-biquinoline N,N‘-Dioxide as an Efficient Catalyst for Enantioselective Addition of Allyltrichlorosilanes to Aldehydes , 1998 .

[19]  Fariati,et al.  X-ray structures of Cu(poph)Cl2, [Cu(pxo)Cl2]2 and [Cu(pxo)(pxo-H)Cl]2 (poph=2-pyridinecarboxaldehyde 1-oxide 2′-pyridinylhydrazone; pxo=2-acetylpyridine 1-oxide oxime). One monomeric structure and two N-oxide-bridged dimeric structures, involving multidentate pyridine N-oxide ligands , 1998 .

[20]  T. Katsuki,et al.  Catalytic asymmetric oxidations using optically active (salen)manganese(III) complexes as catalysts , 1995 .

[21]  R. Noyori,et al.  Asymmetric catalysis in organic synthesis , 1994 .

[22]  I. Ojima,et al.  Catalytic Asymmetric Synthesis , 1993 .

[23]  A. Costa,et al.  Catalytic asymmetric synthesis of homoallylic alcohols , 1993 .

[24]  R. Noyori,et al.  Virtually complete enantioface differentiation in carbonyl group reduction by a complex aluminum hydride reagent , 1979 .