Gold(<scp>I</scp>)‐Catalyzed 5‐<i>endo</i>‐<i>dig</i> Carbocyclization of Acetylenic Dicarbonyl Compounds

Steven T. Staben, Joshua J. Kennedy‐Smith, F. Dean Toste

Angewandte Chemie International Edition · 2004 · 268 citations · 36 references

Concepts

Abstract

Cyclopentenoid structures including compounds containing vinyl iodide, 1,3-diene, and heterocyclic moieties are obtained through the gold(I)-catalyzed 5-endo-dig addition of β-dicarbonyl compounds to unactivated alkynes under neutral conditions and at room temperature (RT). Both monocyclic and bicyclic cyclopentenes can be formed in excellent yields and with good diastereoselectivity (see scheme).

References

36