ol403041k_si_001.pdf (2.89 MB)
Catalytic Conjugate Addition of Acyl Anion Equivalents Promoted by Fluorodesilylation
journal contribution
posted on 2014-01-03, 00:00 authored by Scott E. Denmark, Lindsey R. CullenThe 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 13C NMR spectroscopy
and extension to an asymmetric variant is also presented.