First synthesis and resolution of a planar-chiral tetrahydroindolyl complex of iron: Electronic tuning of reactivity and enantioselective nucleophilic catalysis



The first examples of an (η5-indolyl)iron complex and of an (η5-tetrahydroindolyl)iron complex are described. Reactivity studies establish that the (η5-tetrahydroindolyl)iron complexes are the most active azaferrocene-derived nucleophilic catalysts reported to date and that the reactivity of these complexes can be electronically tuned. Use of planar-chiral, enantiopure (η5-3-(dimethylamino)tetrahydroindolyl)FeCp* in asymmetric catalysis leads to stereoselectivities comparable to those furnished by a previously described azaferrocene complex. Chirality 12:318–324, 2000. © 2000 Wiley-Liss, Inc.