Asymmetric Allylic Substitution in Water with a Polymeric Pd Catalyst

Significance

Asymmetric π-allylic substitution of meso-1,4-diacetoxycycloalkenes was performed with an amphiphilic PS-PEG resin-supported chiral phosphine-palladium complex. Thus, the reaction of cis-1,4-diacetoxycyclopentene (meso-1) with diethyl malonate, dibenzylamine and phenols in water gave the corresponding 1-acetoxy-4-substituted cyclopentenes 2a-i with 90-99% ee in 43-64% yield. Cyclohexenyl ester (meso-4) also underwent etherification with phenol to give 5 in 37% yield (95% ee) and 11% of 6.