Catalytic Conjugate Addition of Acyl Anion Equivalents Promoted by Fluorodesilylation

2014-01-03T00:00:00Z (GMT) by Scott E. Denmark Lindsey R. Cullen
The conjugate addition of acyl anion equivalents derived from 2-silyl-1,3-dithianes to α,β-unsaturated ketones and esters has been achieved using a substoichiometric amount of TBAF. High yields and short reaction times are observed for the addition of aryl-1,3-dithianes to a variety of cyclic and acyclic α,β-unsaturated carbonyl acceptors. Observation of the reactive anion by <sup>13</sup>C NMR spectroscopy and extension to an asymmetric variant is also presented.