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 (eta(5)-indolyl)iron complex and of an (eta(5)-tet rahydroindolyl)iron complex are described, Reactivity studies establish tha t the (eta(5)-tetrahydroindolyl)iron complexes are the most active azaferro cene-derived nucleophilic catalysts reported to date and that the reactivit y of these complexes can be electronically tuned. Use of planar-chiral, ena ntiopure (eta(5)-3- (dimethylamino) tetrahydroindolyl) FeCp* in asymmetric catalysis leads to stereoselectivities comparable to those furnished by a p reviously described azaferrocene complex. (C) 2000 Wiley-Liss, Inc.