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Chiral Cyclopentadienyl Iridium(III) Complexes Promote Enantioselective Cycloisomerizations Giving Fused Cyclopropanes
Author(s) -
Dieckmann Michael,
Jang YunSuk,
Cramer Nicolai
Publication year - 2015
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.201506483
Subject(s) - cyclopentadienyl complex , enantioselective synthesis , iridium , cycloisomerization , chemistry , cyclopropane , ligand (biochemistry) , iodide , counterion , enyne , combinatorial chemistry , stereochemistry , catalysis , medicinal chemistry , organic chemistry , ring (chemistry) , ion , receptor , biochemistry
Abstract The cyclopentadienyl (Cp) group is a very important ligand for many transition‐metal complexes which have been applied in catalysis. The availability of chiral cyclopentadienyl ligands (Cp x ) lags behind other ligand classes, thus hampering the investigation of enantioselective processes. We report a library of chiral Cp x Ir III complexes equipped with an atropchiral Cp scaffold. A robust complexation procedure reliably provides Cp x Ir III complexes with tunable counterions. In a proof‐of‐concept application, the iodide‐bearing members are shown to be highly selective for enyne cycloisomerization reactions. The dehydropiperidine‐fused cyclopropane products are formed in good yields and enantioselectivities.