European Journal of Organic Chemistry · 2010 · 49 citations · 43 references
Natural SciencesChemistryCatalysisOrganometallic ChemistryReaction EngineeringCatalyst DesignCatalytic MaterialsHeterocycle SynthesisMetal CatalysisOrganic SynthesisSolvent-free SynthesisClaisen CondensationClaisen RearrangementMild Reaction ConditionsSilyl Ether DeprotectionTransition Metal-catalyzed Synthesis
Abstract An iron(III) salt catalyzed retro‐Claisen condensation between an alcohol and a 1,3‐diketone was investigated. The mechanism involves the formation of a metal‐induced six‐membered cyclic transition state and cleavage of the C –C bond. Regioselective esterification and one‐pot conversion of silyl ethers into esters with good yields was observed. Simple reaction conditions, high yields, and broad scope of the reaction illustrate the good synthetic utility of this method.
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Andrew G. Myers, Bryant H. Yang, Hou Chen et al. · Journal of the American Chemical Society · 1997 · 563 citations