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Synlett 1991; 1991(5): 331-334
DOI: 10.1055/s-1991-34722
DOI: 10.1055/s-1991-34722
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Regio- and Stereocontrolled Synthesis of Terminal 1,3,5-Triene Monoxides via Diene-Iron Tricarbonyl Complexes
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Publikationsverlauf
Publikationsdatum:
07. März 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.