Chelating Diamide Based Rate Enhancement of Intramolecular Alkene Hydroaminations Catalyzed by a Neutral Sc(III) Complex
- 1 September 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (20) , 4391-4393
- https://doi.org/10.1021/ol051574h
Abstract
Neutral scandium amido complexes are viable catalysts for intramolecular alkene hydroamination. Catalytic activity is strongly coupled to the electronic character of the Sc(III) ligand environment with chelating diamide coordination providing a precatalyst possessing substantially improved activity and superb distereoselectivity in the synthesis of trans-2,5-disubstituted pyrrolidines.Keywords
This publication has 18 references indexed in Scilit:
- New Yttrium Complexes Bearing Diamidoamine Ligands as Efficient and Diastereoselective Catalysts for the Intramolecular Hydroamination of Alkenes and AlkynesOrganometallics, 2004
- Scandium-Catalyzed Intramolecular Hydroamination. Development of a Highly Active Cationic CatalystOrganometallics, 2004
- Synthesis and Characterization of New Biphenolate and Binaphtholate Rare‐Earth‐Metal Amido Complexes: Catalysts for Asymmetric Olefin Hydroamination/CyclizationChemistry – A European Journal, 2003
- Chiral-at-metal organolanthanides: enantioselective aminoalkene hydroamination/cyclisation with non-cyclopentadienylsElectronic supplementary information (ESI) available: complete experimental procedures and characterising data for all ligands and complexes, crystal data for [YL2{N(SiMe2H)2}(THF)] and [SmL4{N(SiMe2H)}]. See http://www.rsc.org/suppdata/cc/b3/b305105f/Chemical Communications, 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
- Constrained Geometry Organolanthanide Catalysts. Synthesis, Structural Characterization, and Enhanced Aminoalkene Hydroamination/Cyclization ActivityOrganometallics, 1999
- Organolanthanide-Catalyzed Hydroamination/Cyclization. Efficient Allene-Based Transformations for the Syntheses of Naturally Occurring AlkaloidsJournal of the American Chemical Society, 1999
- Metal-Initiated Amination of Alkenes and AlkynesChemical Reviews, 1998
- Organolanthanide-catalyzed hydroamination. A kinetic, mechanistic, and diastereoselectivity study of the cyclization of N-unprotected amino olefinsJournal of the American Chemical Society, 1992
- Low co-ordination numbers in lanthanide and actinide compounds. Part I. The preparation and characterization of tris{bis(trimethylsilyl)-amido}lanthanidesJ. Chem. Soc., Dalton Trans., 1973