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A radical-based approach to hydroxytetralones from unprotected phenols
1Laboratoire de Synthèse Organique associé au C.N.R.S., Département de Chimie, Ecole Polytechnique, F-91128 Palaiseau, France.
Chemical Communications (Cambridge, England)
|June 17, 2010
Summary
Xanthates from unprotected 2-hydroxyacetophenones readily add to alkenes, followed by cyclization, yielding valuable hydroxytetralones efficiently.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Xanthate chemistry is crucial for various organic transformations.
- Hydroxytetralones are important structural motifs in natural products and pharmaceuticals.
Purpose of the Study:
- To develop a novel synthetic route to hydroxytetralones.
- To explore the reactivity of xanthates derived from unprotected 2-hydroxyacetophenones.
Main Methods:
- Intermolecular addition of xanthates to unactivated alkenes.
- Subsequent cyclization reactions.
- Utilizing unprotected 2-hydroxyacetophenones as starting materials.
Main Results:
- Smooth intermolecular addition of xanthates to unactivated alkenes was achieved.
- Efficient cyclization to form hydroxytetralones in good yield.
- Demonstrated the utility of unprotected 2-hydroxyacetophenones in this transformation.
Conclusions:
- A new, efficient method for synthesizing hydroxytetralones using xanthates has been established.
- This method offers a valuable tool for accessing complex molecular architectures.
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