Lanthanide Complexes Coordinated by N‐Substituted (R)‐1,1′‐Binaphthyl‐2,2′‐diamido Ligands in the Catalysis of Enantioselective Intramolecular Hydroamination
- 17 May 2005
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 11 (11) , 3455-3462
- https://doi.org/10.1002/chem.200401203
Abstract
A new family of lanthanide ionic complexes derived from chiral, substituted (R)-binaphthylamine ligands, [Li(thf)4][Ln{(R)-C20H12(NR)2}2] (Ln=Yb, Sm, Nd, or Lu), has been synthesized and characterized by X-ray crystal structure analyses. All complexes have been tested as new catalysts for the hydroamination/cyclization of 1-(aminomethyl)-1-allylcyclohexane. Ytterbium complexes proved to be both the most active and the most enantioselective, and the use of the complex [Li(thf)4][Yb{(R)-C20H12(NC3H7)2}2], bearing isopropyl radicals on the nitrogen atoms, allowed the formation of the corresponding spiropyrrolidine in high yield with up to 70 % ee.Keywords
This publication has 73 references indexed in Scilit:
- New Yttrium Complexes Bearing Diamidoamine Ligands as Efficient and Diastereoselective Catalysts for the Intramolecular Hydroamination of Alkenes and AlkynesOrganometallics, 2004
- Enantioselective Catalytic Hydroamination of AlkenesAngewandte Chemie International Edition in English, 2003
- Exceptional Rate Enhancements and Improved Diastereoselectivities through Chelating Diamide Coordination in Intramolecular Alkene Hydroaminations Catalyzed by Yttrium and Neodymium Amido ComplexesAngewandte Chemie International Edition in English, 2002
- Cyclopentadienyl Behavior of Pyrrolyl Anions within the meso-Octaethylporphyrinogen-Binding Lanthanides: Carbon−Hydrogen and Metal−Carbon Bond RearrangementsInorganic Chemistry, 1999
- Metal-Initiated Amination of Alkenes and AlkynesChemical Reviews, 1998
- An η6-Toluene Complex of Neodymium: [Nd(η6-C6H5CH3)(AlCl4)3]Acta Crystallographica Section C Crystal Structure Communications, 1997
- Dilithium diamides [{Li(OC4H8)}2{C20H12(NR)2}](R = SiMe3or CH2But) derived from R-, S- or R,S-2,2′-diamino-1,1′-binaphthyl derivativesJ. Chem. Soc., Dalton Trans., 1996
- Organolanthanide-Catalyzed Carbon-Heteroatom Bond Formation. Observations on the Facile, Regiospecific Cyclization of AminoalkynesOrganometallics, 1994
- The Atom Economy—A Search for Synthetic EfficiencyScience, 1991
- Chemistry of (octaethylporphyrinato)lutetium and -yttrium complexes: synthesis and reactivity of (OEP)MX derivatives and the selective activation of O2 by (OEP)Y(.mu.-Me)2AlMe2Inorganic Chemistry, 1991