Diastereoselective Alkylations of Enolates Directed by Chiral Electrophiles

Significance

The report highlights a novel methodology for constructing fully substituted α-hydroxy carboxylic acids by an electrophile-directed diastereoselective alkylation. The approach uses chiral alkyl iodides with achiral enolates that are converted into dienediolates using a lithium base. Examples with chiral primary and secondary iodides are demonstrated, and an extension to lactone formation is shown.