Additions of aldehydes to metallated trans-1,3-dithiane-S,S-dioxide under conditions of kinetic and thermodynamic control

Article abstract of DOI:10.1016/S0040-4039(00)94354-5

The chiral acyl anion equivalent (1) can be metallated with n-BuLi/py and reacts with aldehydes to give adducts in high yield. At -78°C the reaction is under kinetic control whereas at 0°C equilibration occurs with PhCHO and t-BuCHO resulting in good yields of single diastereoisomers.