Preparation of 2-Lithiotetrahydropyrans: Kinetic and Thermodinamic Generation of Alkyllithium Reagents

Article abstract of DOI:10.1016/S0040-4039(00)99389-4

Both axial and equatorial 2-lithiotetrahydropyrans are readily prepared from 2-(phenylthio)-tetrahydropyrans.Axial 2-lithiotetrahydropyrans are formed selectively on reducing 2-(phenylthio)-tetrahydropyrans with lithium di-tert-butylbiphenylide, and equatorial 2-lithiotetrahydropyrans are formed selectively by thermal equilibration of the axial isomers.