92676-71-6Relevant academic research and scientific papers
A Method for the Preparation of β-Amino-α,β-unsaturated Carbonyl Compounds: Study of Solvent Effect and Mechanism
R. S., Reyno,Sugunan, Akash,S., Ranganayakulu,Suresh, Cherumuttathu H.,Rajendar, Goreti
supporting information, p. 1040 - 1045 (2020/02/15)
An efficient method for the preparation of β-amino-α,β-unsaturated carbonyl compounds is demonstrated. Bench-stable sodium 3-oxo-enolates were prepared from carbonyl compounds, and reacted with amines in the presence of an acid and a desiccant. DFT studie
Microwave-assisted palladium-catalyzed allylation of β-enaminones
Erray, Imen,Rezgui, Farhat,Oble, Julie,Poli, Giovanni
supporting information, p. 2196 - 2200 (2014/11/12)
A new palladium-catalyzed approach for the C-allylation of β-enaminones under microwave irradiation is reported. This methodology provides an easy access to a variety of α-allylated enaminones. The reaction takes place with the preservation of the enamine function, which is poised for further transformations towards nitrogen-containing heterocycles. Georg Thieme Verlag Stuttgart New York.
An efficient approach to Aspidosperma alkaloids via [4 + 2] cycloadditions of aminosiloxydienes: Stereocontrolled total synthesis of (±)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine
Kozmin, Sergey A.,Iwama, Tetsuo,Huang, Yong,Rawal, Viresh H.
, p. 4628 - 4641 (2007/10/03)
Described is a concise, highly stereocontrolled strategy to the Aspidosperma family of indole alkaloids, one that is readily adapted to the asymmetric synthesis of these compounds. The strategy is demonstrated by the total synthesis of (±)-tabersonine (rac-1), proceeding through a 12-step sequence. The basis for this approach was provided by a highly regio- and stereoselective [4 + 2] cycloaddition of 2-ethylacrolein with 1-amino-3-siloxydiene developed in our laboratory. Subsequent elaboration of the initial adduct into the hexahydroquinoline DE ring system was accomplished efficiently by a ring-closing olefin metathesis reaction. A novel ortho nitrophenylation of an enol silyl ether with (o-nitrophenyl)phenyliodonium fluoride was developed to achieve an efficient, regioselective introduction of the requisite indole moiety. The final high-yielding conversion of the ABDE tetracycle into pentacyclic target rac-1 relied on intramolecular indole alkylation and regioselective C-carbomethoxylation. Our approach differs strategically from previous routes and contains built-in flexibility necessary to access many other members of the Aspidosperma family of indole alkaloids. The versatility of the synthetic strategy was illustrated through the asymmetric syntheses of the following Aspidosperma alkaloids: (+)-aspidospermidine, (-)-quebrachamine, (-)-dehydroquebrachamine, (+)-tabersonine, and (+)-16-methoxytabersonine. Of these, (+)-tabersonine and (+)-16-methoxytabersonine were synthesized in greater than 1 -g quantities and in enantiomerically enriched form (～95% ee). The pivotal asymmetry- introducing step was a catalyzed enantioselective Diels-Alder reaction, which proceeded to afford the cycloadducts in up to 95% ee. Significantly, the synthetic sequence was easy to execute and required only four purifications over the 12-step synthetic route.
REACTION OF 1-ETHOXY-1-BUTEN-3-ONE WITH AMINES
Markova, N. K.,Zaichenko, Yu. A.,Tsil'ko, A. E.,Maretina, I. A.
, p. 876 - 880 (2007/10/02)
In the reaction of 1-ethoxy-1-buten-3-one with ammonia and primary and secondary amines the alkoxy group is substituted by an amino group.In the reaction with ammonia 1-amino-1-buten-3-one condenses with the formation of 2-methyl-5-acetylpyridine.
