New preparation of benzylic zinc reagents via a fragmentation reaction

The fragmentation of sterically hindered homobenzylic zinc alcoholates proceeds readily leading to benzylic zinc reagents free from any Wurtz-coupling product. Reaction of these organometallic intermediates with various aldehydes produces new homobenzylic alcohols in moderate to good yields. A 1,4-addition of these newly prepared benzylic organometallics to an alkylidenemalonate is also reported.