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Synlett 1991; 1991(5): 331-334
DOI: 10.1055/s-1991-34722
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Regio- and Stereocontrolled Synthesis of Terminal 1,3,5-Triene Monoxides via Diene-Iron Tricarbonyl Complexes

Michel Franck-Neumann* , Abdelkrim Abdali, Pierre-Jean Colson, Madjid Sedrati
  • *Laboratoire de Chimie Organique Synthetique, Associé au CNRS (URA no 466), Institut de Chimie, Université Louis Pasteur, 1 rue Blaise Pascal, F-67008 Strasbourg, France
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Publication Date:
07 March 2002 (online)

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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.

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