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Enantioselective Gold Catalysis: Opportunities Provided by Monodentate Phosphoramidite Ligands with an Acyclic TADDOL Backbone
Author(s) -
Teller Henrik,
Flügge Susanne,
Goddard Richard,
Fürstner Alois
Publication year - 2010
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.200906550
Subject(s) - phosphoramidite , denticity , enantioselective synthesis , ligand (biochemistry) , chemistry , catalysis , combinatorial chemistry , acetal , stereochemistry , organic chemistry , crystal structure , receptor , dna , biochemistry , oligonucleotide
The tail makes the difference : Removing the isopropylidene acetal unit from well‐known TADDOL ligands improved the performance of the derived phosphoramidite ligands in asymmetric gold catalysis (see scheme; Ts=4‐toluenesulfonyl). X‐ray crystallography showed that the binding pocket has an effective threefold symmetry, with through‐space interactions between the arene rings of the ligand and the gold center.