553670-66-9Relevant articles and documents
A synthesis of α-lithiated enol ethers from α-arenesulfinyl enol ethers: Ni(0)- and Pd(0)-catalysed coupling of enol triflates and phosphates derived from lactones with sodium arenethiolates gives α-arenesulfanyl enol ethers
Milne, Jacqueline E.,Kocienski, Philip J.
, p. 584 - 592 (2007/10/03)
A three-step synthesis of stable and storable α-benzene-sulfinyl enol ethers from lactones entails (a) conversion of a lactone to an enol triflate or phosphate; (b) Ni(0) and Pd(0) cross-coupling of the enol triflate or phosphate with a sodium arenethiolate to give an α-arenethio enol ether; and (c) oxidation of an arenethio group to a sulfoxide. The α-benzenesulfinyl enol ethers undergo sulfoxide-lithium exchange on reaction with n-BuLi to give α-lithiated enol ethers thus making the α-benzenesulfinyl group a surrogate for the trialkylstannyl group which has hitherto served as the most common precursor to α-lithiated enol ethers.
