β-Functionalised Organolithium Compounds through a Sulfur-lithium Exchange

Abstract

The successive reaction of different β-hydroxy or β-amino thioethers 1a-d with n-butyl-lithium and an excess of lithium powder and a catalytic amount of DTBB in THF at −78°C leads to the formation of the corresponding β-functionalised organolithium compounds 2a-d, which by reaction with several electrophiles [D2O, ButCHO, PhCHO, Me2CO, (CH2)5CO] at temperatures ranging between −78 and 20°C yields, after hydrolysis with water, the expected functionalised alcohols or amines 3aa-de in a regioselective manner.