Enantioselective Synthesis of 4‑Heterosubstituted
Cyclopentenones

Reiser, Oliver

Enantioselective Synthesis of 4‑Heterosubstituted Cyclopentenones

Posted on 2013-04-19 - 00:00

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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Ulbrich, Kathrin; Kreitmeier, Peter; Vilaivan, Tirayut; Reiser, Oliver (2016). Enantioselective Synthesis of 4‑Heterosubstituted Cyclopentenones. ACS Publications. Collection. https://doi.org/10.1021/jo400409f

https://doi.org/10.1021/jo400409f

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