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

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Abstract

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-FeII complexes having metal- and ligand-centered chirality. The cis-β FeII(N4) complex [FeII(L)(OTf)2] (L = N,N′-bis(2,3-dihydro-1H-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 >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.

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Wei, J., Cao, B., Tse, C. W., Chang, X. Y., Zhou, C. Y., & Che, C. M. (2020). Chiral: Cis -iron(ii) complexes with metal- And ligand-centered chirality for highly regio- And enantioselective alkylation of N-heteroaromatics. Chemical Science, 11(3), 684–693. https://doi.org/10.1039/c9sc04858h

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