97060-53-2Relevant academic research and scientific papers
Cerium(III) amide enolate. Addition of propionamide to conjugated enones
Shang,Liu
, p. 2155 - 2159 (2007/10/02)
The cerium(III) enolate of propionamide 1 was found to undergo preferential 1,2-addition with most of the sterically hindered conjugated enones studied. The effects of HMPA and 12-crown-4 on the regioselectivity were also investigated.
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.
Stereoselection in the Michael Addition Reaction. 2. Stereochemistry of the Kinetic Michael Reaction of Amide Enolates with Enones
Heathcock, Clayton H.,Henderson, Mark A.,Oare, David A.,Sanner, Mark A.
, p. 3019 - 3022 (2007/10/02)
An extensive study of structure-stereoselectivity relationships in the kinetic Michael addition of preformed lithium enolates to enones has uncovered some reactions of sufficiently high diastereoselectivity as to be synthetically attractive and has allowe
