Palladium-catalysed allylic sulphinate–sulphone rearrangements; asymmetric induction in the palladium-catalysed transfer of chiral sulphinates to sulphones

Abstract

The rearrangement of allylic sulphinates to sulphones is facilitated by palladium catalysis, treatment of the chiral trans-and cis-allyl sulphinates (S)-(–)-(1a)-(1c), and -(1e), and(S)-(–)-(1b)and -(1d)with a catalytic amount of the palladium catalysts (3)and(5)providing the corresponding chiral allyl sulphones,(S)-(+)-and(R)-(–)-(2a–c), respectively, in good yields; exceptionally the palladium catalysis of the rearrangement of (S)-(–)-(1f)produced (S)-(+)-(2c).