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.
Direct Catalytic Desaturation of Lactams Enabled by Soft Enolization
Chen, Ming,Dong, Guangbin
supporting information, p. 7757 - 7760 (2017/06/21)
A direct catalytic method is described for the α,β-desaturation of N-protected lactams to their conjugated unsaturated counterparts under mildly acidic conditions. The reaction is consistently operated at room temperature and tolerates a wide range of functional groups, showing reactivity complementary to that of prior desaturation methods. Lactams with various ring sizes and substituents at different positions all reacted smoothly. The synthetic utility of this method is demonstrated in a concise synthesis of Rolipram. In addition, linear amides also prove to be competent substrates, and the phthaloyl-protected product serves as a convenient precursor to access various conjugated carboxylic acid derivatives. Strong bases are avoided in this desaturation approach, and the key is to merge soft enolization with a Pd-catalyzed oxidation process.
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.
