jo400409f_si_002.cif (30.76 kB)
Download fileEnantioselective Synthesis of 4‑Heterosubstituted Cyclopentenones
dataset
posted on 2013-04-19, 00:00 authored by Kathrin Ulbrich, Peter Kreitmeier, Tirayut Vilaivan, Oliver ReiserRacemic 4-hydroxycyclopentenone,
readily derived from furfuryl
alcohol, can be transformed via its O-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 ent-noraristeromycin
was readily accomplished.