Pseudoephedrine as a Chiral Auxiliary for Asymmetric Michael Reactions: Synthesis of 3-Aryl-δ-lactones

Abstract
The asymmetric Michael reaction of pseudoephedrine amides is reported. The 1,5-dicarbonyl products are converted to 3-aryl-δ-lactones in a two-step reduction/lactonization sequence. This method provides access to enantiomerically enriched trans-3,4-disubstituted δ-lactones.