440357-54-0Relevant academic research and scientific papers
Lewis Acid Enabled Copper-Catalyzed Asymmetric Synthesis of Chiral β-Substituted Amides
Rodríguez-Fernández, Mamen,Yan, Xingchen,Collados, Juan F.,White, Paul B.,Harutyunyan, Syuzanna R.
supporting information, p. 14224 - 14231 (2017/10/17)
Here we report that readily available silyl- and boron-based Lewis acids in combination with chiral copper catalysts are able to overcome the reactivity issues of unactivated enamides, known as the least reactive carboxylic acid derivatives, toward alkyla
Aldol condensation of amides using phosphazene-based catalysis
Foo, Siong Wan,Oishi, Shun,Saito, Susumu
, p. 5445 - 5448 (2012/10/29)
We have developed a new method for the direct aldol condensation of unactivated amides using 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6- hexachloride (TAPC)-based phosphorous/SO42- catalysis. The SO42- species in a reaction mixture enhances the reaction rate of the catalysis. In principle, no metal sources are required for the generation of the catalyst, and there is no requirement for the use of stoichiometric quantities of an acid or base. This catalyst system is operative under relatively acidic conditions. One major advantage of carrying out the reaction under acidic conditions is that both aldehydes and acetals are capable of undergoing carbon-carbon bond formation at the α-carbon of amide carbonyl groups through dehydration.
Z-selective synthesis of α,β-unsaturated amides with triphenylsilylacetamides
Kojima, Satoshi,Inai, Hiroki,Hidaka, Tsugihiko,Fukuzaki, Tomohide,Ohkata, Katsuo
, p. 4093 - 4099 (2007/10/03)
With the purpose of developing a method of preparing Z-α,β-unsaturated amides, the Peterson reaction of the (triphenylsilyl)acetamide Ph3SiCH2COX (1, X = NBn2; 3, X = NMe2) with various aldehydes was examined. The reaction of aromatic aldehydes gave selectivities up to >97:3. It was found that the selectivity was a function of the electronic nature of the aromatic ring and higher Z selectivity was attained with electron-rich aldehydes. With aliphatic aldehydes selectivities up to 92:8 were achieved, and unlike with analogous phosphorus reagents, less sterically hindered aldehydes gave higher Z selectivity. Also, 3, which has a smaller amide group than 1, tended to give rise to higher selectivity. A comparison with the reaction of trimethylsilyl analogues revealed the significance of the phenyl substituents on the silyl group.
