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DOI: 10.1055/s-1990-21196
An Efficient and Simple Synthesis of Functionalized and Unfunctionalized Enantiomerically Pure Diene-Iron Tricarbonyl Complexes
Publication History
Publication Date:
08 March 2002 (online)
The esters of 2,4-alkadienoic acids with S-(-)-ethyl lactate, obtained either by direct esterification or via Horner-Emmons olefination with the optically active phosphonate 3 [ethyl 2-(diethoxyphosphorylacetoxy)propanoate], give diastereomeric diene-iron tricarbonyl complexes [tricarbonyl(1-ethoxycarbonyl-ethyl 2-5-η-alka-2,4-dienoate)iron]. These are easily separated by simple silica gel chromatography and readily transformed into the optically active diene complexes (methyl esters) 6 [tricarbonyl-(methyl 2-5-η-alka-2,4-dienoate)iron] and (unfunctionalized dienes) 7 [tricarbonyl(2-5-η-alka-2,4-diene)iron] both of high optical purity. The absolute configuration of a number of these complexes could be attributed on the basis of chemical correlations.