Palladium-Catalyzed Site-Differentiative Coupling of a Chiral Cyclopentenol Derivative with Racemic 3-Hydroxyalkenyl Iodide: New Chemical Resolution of 4-Alkenyl-3-hydroxy- cyclopentanones

Torii, S.; Okumoto, H.; Kotani, T. Synlett 1992, 349.

Optically active mono-protected 2-cyclopentene-1,4-diol(+)-1 was site-selectively coupled with (Z)-3-tert-butyldimethylsiloxy-1-octenyl iodide [2] in the presence of a palladium catalyst, followed by separation and acid treatment to give (+)-and (-)-3-hydroxy-4-(3-hydroxy-1-octenyl)cyclopentanone[(+)-6 and (-)-6] in pure form.