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Chemistry. 2016 Feb 24;22(9):3065-72. doi: 10.1002/chem.201504458. Epub 2016 Jan 25.

Enantiopure Ferrocene-Based Planar-Chiral Iridacycles: Stereospecific Control of Iridium-Centred Chirality.

Author information

1
School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, NR4 7TJ, UK.
2
Department of Chemistry, Karakoram International University, University Road, Gilgit-, 15100, Pakistan.
3
EPSRC National Crystallography Service, School of Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, UK.
4
School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, NR4 7TJ, UK. Chris.Richards@uea.ac.uk.

Abstract

Reaction of [IrCp*Cl2 ]2 with ferrocenylimines (Fc=NAr, Ar=Ph, p-MeOC6 H4 ) results in ferrocene C-H activation and the diastereoselective synthesis of half-sandwich iridacycles of relative configuration Sp *,RIr *. Extension to (S)-2-ferrocenyl-4-(1-methylethyl)oxazoline gave highly diastereoselective control over the new elements of planar chirality and metal-based pseudo-tetrahedral chirality, to give both neutral and cationic half-sandwich iridacycles of absolute configuration Sc ,Sp ,RIr . Substitution reactions proceed with retention of configuration, with the planar chirality controlling the metal-centred chirality through an iron-iridium interaction in the coordinatively unsaturated cationic intermediate.

KEYWORDS:

chirality; enantioselectivity; ferrocene; iridacycle; stereoselectivity

PMID:
26809030
DOI:
10.1002/chem.201504458

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