Enantioselective Synthesis of 4‑Heterosubstituted Cyclopentenones

Racemic 4-hydroxycyclopentenone, readily derived from furfuryl alcohol, can be transformed via its <i>O</i>-Boc derivative to 4-acyloxy, 4-aryloxy-, 4-amino-, or 4-thio-substituted cyclopentenones with high enantioselectivity by palladium-catalyzed kinetic resolution via nucleophilic allylic substitutions. Applying this methodology, a short formal synthesis of <i>ent</i>-noraristeromycin was readily accomplished