Cross metathesis reactions of homoallylmethyl malonates with sterically hindered allylic esters

The methyl malonate esters of 3-buten-1-ol and 2-methyl-3-buten-1-ol can be coupled efficiently with different methallylic esters in presence of the second generation Grubbs catalyst to yield trisubstituted olefins from the cross metathesis reaction. Product selectivity and yields depend on the relative feedstock stoichiometries and not by the methallylic ester functional group. Alkyl substituents at either the allylic or the geminal position affect significantly the product yields and the E/Z stereoselectivity.