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Enantioselective Alkynylbenzaldehyde Cyclizations Catalyzed by Chiral Gold(I) Acyclic Diaminocarbene Complexes Containing Weak Au–Arene Interactions
Author(s) -
Handa Sachin,
Slaughter LeGrande M.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201107789
Subject(s) - cycloisomerization , enantioselective synthesis , catalysis , chirality (physics) , chemistry , stereochemistry , substrate (aquarium) , combinatorial chemistry , organic chemistry , physics , chiral symmetry , oceanography , quantum mechanics , geology , nambu–jona lasinio model , quark
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.