β-Functionalised organolithium compounds through a sulfur-lithium exchange

Article abstract of DOI:10.1016/S0040-4039(97)01008-3

The successive reaction of different β-hydroxy or β-amino tbioethers 1a-d with n-butyl-lithium and an excess of lithium powder and a catalytic amount of DTB 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, Bu(t)CHO, 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.