26487-93-4Relevant academic research and scientific papers
Stereochemistry of the Michael Addition of N,N-Disubstituted Amide and Thioamide Enolates to α,β-Unsaturated Ketones
Oare, David A.,Henderson, Mark A.,Sanner, Mark A.,Heathcock, Clayton H.
, p. 132 - 157 (2007/10/02)
A systematic study of the regio- and diastereoselectivity of the kinetic Michael addition of amide and thioamide enolates to a series of α,β-unsaturated ketones has been carried out.Factors that influence the diastereo- and regiochemical outcome of the reaction include the substitution pattern of the enone and enolate, the enolate counterion, and the solvent.Numerous examples of high selectivity have been discovered.In a number of examples, either the syn or the anti addition products can be obtained by varying the nature of the solvent, donor atom, and/or counterion.These results have correlated in terms of a coherent transition-state model.
