Enantioselective Alkynylbenzaldehyde Cyclizations Catalyzed by Chiral Gold(I) Acyclic Diaminocarbene Complexes Containing Weak Au–Arene Interactions


  • Financial support for this work was provided by the U.S. National Science Foundation (CAREER Award CHE-0645438). We thank Prof. Tom Cundari (Univ. of North Texas) for computational advice.


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Hold me close: Highly enantioselective catalysis of tandem acetalization/cycloisomerization reactions of o-alkynylbenzaldehydes has been achieved using gold complexes of chiral acyclic diaminocarbene ligands that have electron-deficient aryl substituents. X-ray crystallography and DFT calculations implicate weak gold-arene interactions—absent in the case of simple phenyl substituents—that define the chirality of the substrate binding site.