American Chemical Society
jo400409f_si_002.cif (30.76 kB)

Enantioselective Synthesis of 4‑Heterosubstituted Cyclopentenones

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posted on 2013-04-19, 00:00 authored by Kathrin Ulbrich, Peter Kreitmeier, Tirayut Vilaivan, Oliver Reiser
Racemic 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.