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Iron-catalyzed highly regio- and enantioselective organic transformations with generality and broad substrate scope have profound applications in modern synthetic chemistry; an example is herein described based on cis -Fe II complexes having metal- and ligand-centered chirality. The cis -β Fe II (N 4 ) complex [Fe II (L)(OTf) 2 ] (L = N , N '-bis(2,3-dihydro-1 H -cyclopenta-[ b ]quinoline-5-yl)- N , N '-dimethylcyclohexane-1,2-diamine) is an effective chiral catalyst for highly regio- and enantioselective alkylation of N-heteroaromatics with α,β-unsaturated 2-acyl imidazoles, including asymmetric N1, C2, C3 alkylations of a broad range of indoles (34 examples) and alkylation of pyrroles and anilines (14 examples), all with high product yields (up to 98%), high enantioselectivity (up to &gt;99% ee) and high regioselectivity. DFT calculations revealed that the "chiral-at-metal" cis -β configuration of the iron complex and a secondary π-π interaction are responsible for the high enantioselectivity.

chemical science

Chiral <i>cis</i>-iron(<scp>ii</scp>) complexes with metal- and ligand-centered chirality for highly regio- and enantioselective alkylation of N-heteroaromatics

Chiral cis-iron(ii) complexes with metal- and ligand-centered chirality for highly regio- and enantioselective alkylation of N-heteroaromatics