109299-93-6Relevant articles and documents
Synthesis of α,β-unsaturated amides by olefin cross-metathesis
Choi, Tae-Lim,Chatterjee, Arnab K.,Grubbs, Robert H.
, p. 1277 - 1279 (2001)
Electronic and steric properties of the substituents on the amide nitrogen atom govern the yield and rate of the cross-metathesis between a variety of αβ-unsaturated amides and olefins with 1 as the catalyst. This influence is the result of deactivation of the catalyst by chelation of the carbonyl group to the metal. However, an increase in catalyst loading compensates for the chelation effect.
Asymmetric FeII-Catalyzed Thia-Michael Addition Reaction to α,β-Unsaturated Oxazolidin-2-one Derivatives
Lauzon, Samuel,Keipour, Hoda,Gandon, Vincent,Ollevier, Thierry
supporting information, p. 6324 - 6327 (2017/12/08)
A highly enantioselective FeII-catalyzed thia-Michael addition to α,β-unsaturated carbonyl derivatives was developed. The scope of the reaction was demonstrated with a selection of aromatic, heterocyclic and aliphatic thiols, and various Michael acceptors. The corresponding β-thioethers were obtained in good to excellent yields (up to 98%) and moderate to excellent enantioselectivities (up to 96:4 er). Unusual hepta-coordination of the metal and chelation to α,β-unsaturated oxazolidin-2-one derivatives allowed the construction of a coherent model rationalizing the enantioselective event. DFT calculations support the proposed model for observed stereoselectivities.
Lanthanide Lewis acid-mediated enantioselective conjugate radical additions
Sibi, Mukund P.,Manyem, Shankar
, p. 2929 - 2932 (2007/10/03)
(figure presented) Lanthanide triflates along with proline-derived ligands have been found to be efficient catalysts for enantioselective conjugate addition of nucleophilic radicals to enoates. N-Acyl oxazolidinones, when used as achiral additives, gave meaningful enhancements in the ees for the product.
