The diastereoselective synthesis of trans-2-substituted vinylcyclopentanes is described. The method is based on the intramolecular coupling of 7-methoxy-1,5-dienes involving a sequential activation of the C═C double bonds via hydrozirconation and TMSOTf-promoted allylation.
A formal [4+1]-annulation strategy between sulfur ylides and 1,3-dienes was developed to afford functionalized cyclopentanoids. The process consists of a stereoselective cyclopropanation reaction followed, in situ, by a stereospecific MgI -catalyzed vinylcyclopropane-cyclopentene rearrangement. The use of chiral sulfur ylides provided cyclopentanoids with excellent enantiocontrol. A combined experimental and computational mechanistic study showed that the stereospecificity of the rearrangement could be accounted for by a double S 2 reaction mechanism involving iodide.
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