The combination of domino process and kinetic resolution: organocatalytic synthesis of functionalised cyclopentenes by sequential SN2′-Michael reaction

An interesting combination of organocatalytic cascade reaction and kinetic resolution was developed for the synthesis of functionalised cyclopentenes by sequential SN2′-Michael process. Treatment of the racemic nitroallylic acetates with glutaraldehyde in the presence of diphenylprolinol silyl ether to give tetrasubstituted cyclopentenes with high to excellent stereoselectivities (up to 96% ee and 12:1 dr). The less reactive enantiomeric substrates were generally recovered with good to excellent optical purities (up to 99% ee).