1,5-Asymmetric induction of chirality: highly diastereoselective addition reactions of organoaluminium reagents into ketone groups in the side-chain of π-allyltricarbonyliron lactone complexes

Abstract

The utility of π-allyltricarbonyliron lactone complexes has been extended to include their use as chiral auxiliaries. Organoaluminium reagents add into ketone groups positioned in the side-chain of the allyl ligand to afford the corresponding tertiary alcohol complexes in good to excellent yield and with excellent diastereocontrol. Enantiomerically enriched complexes can be synthesised using the Sharpless asymmetric epoxidation protocol as the source of chirality. Addition products derived from endo ketones can be converted into the corresponding (E,E )-η⁴-dienetricarbonyliron complexes upon treatment with barium hydroxide solution without loss of diastereo- or enantio-purity.

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