Enantiomerically enriched 2,3 disubstituted cyclopentanones were prepared via copper-catalyzed 1,4-reduction of 3-substituted cyclopentenones followed by alkylation of the resulting silyl enol ether. Using this procedure, trans-2,3-disubstituted cyclopentanones were produced in moderate to good overall yields (42-67%) and with excellent enantiomeric and diastereomeric excesses. The reduction and alkylation were performed in a single reaction vessel.
“One-Pot Synthesis of Enantiomerically Enriched 2,3-Disubstituted Cyclopentanones via Copper-Catalyzed 1,4-Reduction and Alkylation”, Org. Lett., 2001, 3(8), 1129-1131.