Journal of Organic Chemistry p. 4202 - 4206 (2013)
Update date:2022-09-26
Topics:
Ulbrich, Kathrin
Kreitmeier, Peter
Vilaivan, Tirayut
Reiser, Oliver
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.
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