Chiral organometallic reagents. Part XXV. The stereochemistry of the ring opening of cyclopropylallyllithium compounds

Abstract

The ring opening of the cyclopropylallyllithium compounds 19 and 34 to give the α-durylhomoallyllithium compounds 20 has been shown to proceed at −107 °C with ≥90% of stereochemical purity. The resulting α-durylthioalkyllithium compounds are configurationally stable at that temperature. They racemize at −78 °C with a half life of 90 min.