78064-73-0Relevant academic research and scientific papers
Chemistry of Substituted cuprates and Their Synthetic Application to Cyclopentenone Annulations
Marino, Joseph Paul,Linderman, Russell J.
, p. 3696 - 3702 (1981)
The conjugate addition of mixed alkyl cuprates to ethyl propiolate generates substituted cuprates that readily react with acid chlorides of α,β-unsaturated acids to produce α,α'-dienones.These unsaturated ketones bearing an α-carboethoxy group can serve as precursors to annulated cyclopentenones via a Nazarov-type cyclization.With this two-step sequence, it is possible to efficiently prepare substituted cyclopentenones fused to five-, six-, and seven-membered rings.As part of an effort to optimize yields in the Nazarov cyclizations, trimhylsilyl iodide was shown to be a new and effective reagent for this transformation.
