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Enantioselective synthesis of 4-heterosubstituted cyclopentenones.

Enantioselective synthesis of 4-heterosubstituted cyclopentenones.

The Journal of organic chemistry (2013-04-03)

Kathrin Ulbrich, Peter Kreitmeier, Tirayut Vilaivan, Oliver Reiser

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.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Tetrahydrofurfuryl alcohol, 98%

Sigma-Aldrich

2-Cyclopenten-1-one, 98%

Sigma-Aldrich

Tetrahydrofurfuryl alcohol, 99%

Sigma-Aldrich

Tetrahydrofurfuryl alcohol, ≥98%

Sigma-Aldrich

Palladium, nanopowder, <25 nm particle size (TEM), ≥99.5%

Sigma-Aldrich

Palladium, powder, 99.995% trace metals basis

Sigma-Aldrich

Palladium, evaporation slug, diam. × L 0.6 cm × 0.6 cm, 99.95% trace metals basis

Sigma-Aldrich

Palladium, powder or granules, 99.99% trace metals basis

Sigma-Aldrich

Palladium, powder, <75 μm, 99.9% trace metals basis

Sigma-Aldrich

Palladium, wire, diam. 0.5 mm, 99.9% trace metals basis

Sigma-Aldrich

Palladium, foil, thickness 1.0 mm, 99.9% trace metals basis

Sigma-Aldrich

Palladium, foil, thickness 0.25 mm, 99.98% trace metals basis

Sigma-Aldrich

Palladium, sponge, 99.9% trace metals basis

Sigma-Aldrich

Palladium, foil, thickness 0.025 mm, 99.9% trace metals basis

Sigma-Aldrich

Palladium, wire, diam. 1.0 mm, 99.9% trace metals basis

Sigma-Aldrich

Palladium, powder, <1 μm, ≥99.9% trace metals basis

Sigma-Aldrich

Palladium, foil, thickness 0.5 mm, 99.9% trace metals basis