Preparative Organic Chemistry
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ChemInform Abstract: Stereoselective Synthesis of (E)-α-Hydroxy-1,3-dienes via the Reaction of 2,5-Dihydrothiophene S,S-Dioxides with Carbonyl Compounds.
First published: September 22, 1987
Abstract
The dihydrothiophene-S,S-dioxides (I) are coupled with the aldehydes and ketones (II) in the presence of a base, yielding the alcohols (III) and (IV) or the ketones (V) which are obtained from methyl vinyl ketone.
ChemInform Abstract
The dihydrothiophene-S,S-dioxides (I) are coupled with the aldehydes and ketones (II) in the presence of a base, yielding the alcohols (III) and (IV) or the ketones (V) which are obtained from methyl vinyl ketone. Desulfonation of (III) - (V) produces the dienes (VI), (VII), and (VIII). The triene (IX) and (E)-tagetone (X) are prepared by dehydration and subsequent desulfonation or oxidation.
