Instantaneous SmI2/H2O/Amine‐Mediated Reductions in THF
- 21 February 2003
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 9 (5) , 1123-1128
- https://doi.org/10.1002/chem.200390129
Abstract
The SmI2-mediated reductions of ketones, imines, and α,β-unsaturated esters have been shown to be instantaneous in the presence of H2O and an amine in THF. The SmI2-mediated reductions are not only shown to be fast and quantitative by the addition of H2O and an amine, but the workup procedures are also simplified. Competing experiments with SmI2/H2O/amine confirmed that α,β-unsaturated esters could be selectively reduced in the presence of ketones or imines. Comparison of analogue ligands showed that nitrogen and phosphorus ligands are superior to oxygen and sulfur ligands in these reductions. The trialkylphosphine 1,2-bis(dimethylphosphino)ethane (DMPE) provided a primary kinetic isotope effect, yielding a kH/kD of 4.5.Keywords
This publication has 34 references indexed in Scilit:
- Recent developments in lanthanide mediated organic synthesisJournal of the Chemical Society, Perkin Transactions 1, 2001
- Isolation, X-ray Structural Characterization, and Reactivities of Diiodosamarium(II) Complexes Bearing Amide Compounds as LigandsBulletin of the Chemical Society of Japan, 2001
- Asymmetric Synthesis of β-Amino Alcohols by Cross-Pinacol Coupling of Planar Chiral Ferrocenecarboxaldehydes with IminesJournal of the American Chemical Society, 2000
- New Sequential Reactions with Single‐Electron‐Donating AgentsAngewandte Chemie International Edition in English, 1997
- Neue sequentielle Reaktionen mit Ein‐Elektronen‐Donor‐ReagentienAngewandte Chemie, 1997
- Stereoselective Cyclization of cis-Decalin Skeleton of Vinigrol via Ketyl-Olefin Coupling Promoted by Samarium(II) IodideSynlett, 1996
- Sequenced Reactions with Samarium(II) Iodide. Tandem Nucleophilic Acyl Substitution/Ketyl−Olefin Coupling ReactionsJournal of the American Chemical Society, 1996
- Application of lanthanide reagents in organic synthesisChemical Reviews, 1992
- Samarium diiodide - A versatile reagent in organic synthesis.Journal of Synthetic Organic Chemistry, Japan, 1989
- Relative Asymmetric Induction in Formation of Substituted Cyclopentanols Via Intramolecular Carjbonyl AdditionsSynthetic Communications, 1987