Intramolecular Nucleophilic Acyl Substitution Reactions Mediated by Samarium(II) Iodide: A Convergent Approach to the Preparation of Enantiomerically Enriched 4-Hydroxy Ketones from 3-Iodopropyl Carboxylates

Article abstract of DOI:10.1021/jo00091a039

Intramolecular nucleophilic acyl substitution (I NAS) reactions of substituted δ-iodopropylcarboxylates have been achieved using samarium(II) iodide (SmI2) in the presence of an iron(III) catalyst.Diverse ester starting materials containing stereogenic centers placed in varying postions on the substrates have been converted to acyclic 4-hydroxy ketone derivatives in good yields using this method.No racemization of stereogenic centers α to the carbonyl was observed in any of the reactions examined.Consequently, the method serves as a convenient, high-yield synthesis of functionalized, enantiomerically enriched acyclic ketones possesing stereogenic centers far removed from one another.