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Synlett 1991; 1991(5): 331-334
DOI: 10.1055/s-1991-34722
DOI: 10.1055/s-1991-34722
letter
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Regio- and Stereocontrolled Synthesis of Terminal 1,3,5-Triene Monoxides via Diene-Iron Tricarbonyl Complexes
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Publication Date:
07 March 2002 (online)
Functionalized and unfunctionalized conjugated dieneiron tricarbonyl complexes are transformed into adjacent diene halohydrins by regio- and stereoselective Friedel-Crafts type acylations, followed by stereoselective reduction. By cyclization, terminal monoxides of conjugated trienes are obtained as complexed or uncomplexed molecules in the racemic or optically active forms. The easy separation and equilibration of diastereoisomeric halodienone complexes allows the synthesis of cis- or trans-epoxides, while the E or Z configuration of the adjacent C=C double bond can be controlled in the acylation step.