Regioselective Synthesis of Trisubstituted Cyclopentadienyl Ligands from Furans

Abstract

1,2,3- And 1,2,4-trisubstituted cyclopentadienyl manganese tricarbonyl compounds have been synthesized regioselectively from furans following a common synthetic strategy. The key steps include the transformation of furylcarbinols into hydroxycyclopentenones followed by the conjugate addition of Grignard reagents under chelation directed conditions. This affords hydroxycyclopentanones which can be dehydrated to cyclopentenones. These compounds are further elaborated into the final targets by the 1,2-addition of organolithium reagents