Journal of Organic Chemistry 2013-04-19

Enantioselective synthesis of 4-heterosubstituted cyclopentenones.

Kathrin Ulbrich, Peter Kreitmeier, Tirayut Vilaivan, Oliver Reiser

Index: J. Org. Chem. 78(8) , 4202-6, (2013)

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Abstract

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.