1248337-48-5Relevant academic research and scientific papers
Fully diastereoselective synthesis of polysubstituted, functionalized piperidines and decahydroquinolines based on multicomponent reactions catalyzed by cerium(IV) ammonium nitrate
Suryavanshi, Padmakar A.,Sridharan, Vellaisamy,Maiti, Swarupananda,Menendez, J. Carlos
, p. 8791 - 8799 (2014)
The cerium(IV) ammonium nitrate (CAN)-catalyzed, three-component reaction between primary amines, β-dicarbonyl compounds, and α,β- unsaturated aldehydes in ethanol heated to reflux, constitutes a general, one-pot synthesis of 1,4-dihydropyridines. Their reduction with sodium triacetoxyborohydride furnished piperidine derivatives bearing up to five substituents with full diastereoselectivity in a hitherto inaccessible stereochemical arrangement. The reaction proceeded with no significant loss of enantiomeric purity under mild reduction conditions that are compatible with several functional groups that are normally sensitive to reduction. Octahydroquinolin-5-one derivatives, which were prepared by a modified version of the initial multicomponent reaction, were not suitable substrates for the sodium triacetoxyborohydride mediated reduction, but they were transformed into the corresponding decahydroquinolines, including a precursor of the amphibian alkaloid pumiliotoxin C, by catalytic hydrogenation under a variety of conditions.
Enantioselective organocatalytic aza-ene-type domino reaction leading to 1,4-dihydropyridines
Noole, Artur,Borissova, Maria,Lopp, Margus,Kanger, Tonis
, p. 1538 - 1545 (2011/06/11)
A new general methodology was developed to access highly enantiomerically enriched 1, 4-dihydropyridines (DHPs) 3 via an organocatalytic asymmetric aza-ene-type cascade reaction, cocatalyzed by (S)-diarylprolinol-TMS ether V and benzoic acid (BA). Both aliphatic and aryl enals 1 reacted smoothly with enaminones and ss-enamino esters 2, affording highly functionalized 1,4-DHPs 3 in high enantioselectivities and good yields. 2011 American Chemical Society.
Br?nsted acid-thiourea co-catalysis: Asymmetric synthesis of functionalized 1,4-dihydropyridines from β-enamino esters and α,β-unsaturated aldehydes
Yoshida, Kohzo,Inokuma, Tsubasa,Takasu, Kiyosei,Takemoto, Yoshiji
experimental part, p. 1865 - 1869 (2010/10/18)
A Br?nsted acid and a novel thiourea derivative co-catalyze the addition of β-enamino esters to α,β-unsaturated aldehydes leading to functionalized 1,4-dihydropyridines with moderate to good enantioselectivity. A regioselective synthesis of 1,2-dihydropyridines from α,β-unsaturated aldehydes is also described. Georg Thieme Verlag Stuttgart.
Catalytic asymmetric synthesis of both enantiomers of 4-substituted 1,4-Dihydropyridines with the use of bifunctional Thiourea-Ammonium salts bearing different counterions
Yoshida, Kohzo,Inokuma, Tsubasa,Takasu, Kiyosei,Takemoto, Yoshiji
experimental part, p. 8305 - 8326 (2011/03/17)
Organoammonium salts composed of a Bronsted acid and an anilinothiourea promoted the Michael addition of β-keto esters and α,β-unsaturated aldehydes in the presence of primary amines to give functionalized 1,4-dihydropyridines enantioselectively. With the
