147779-02-0Relevant articles and documents
Visible Light-Mediated Synthesis of Enantiopure γ-Cyclobutane Amino and 3-(Aminomethyl)-5-phenylpentanoic Acids
Kerres, Sabine,Plut, Eva,Malcherek, Simon,Rehbein, Julia,Reiser, Oliver
, (2019/02/07)
A visible light-mediated [2+2] photocycloaddition of amide-linked dienes using [Ir(dtb-bpy)(dF(CF3)ppy)2]PF6 as triplet sensitizer was applied to generate a variety of N-tert-butyl, N-benzyl- and N-tert-butoxycarbonyl-protected 3-azabicyclo[3.2.0]heptan-2-ones in good yields and with good diastereoselectivity. Density functional theory calculations shed light on the conformational prerequisites for the [2+2] photocycloaddition. The bicyclic key structures could be readily transformed into γ-cyclobutane amino acids. For the obtained racemic 3-phenyl-2-aminocyclobutane-1-carboxylic acid the resolution with chiral oxazolidin-2-one is demonstrated to allow access to both enantiomers. Alternatively, a chiral auxiliary approach led as well to the enantiomerically pure target compound. Finally, the synthesis of either enantiomer of 3-(aminomethyl)-5-phenylpentanoic acid, the racemate being described as an anticonvulsant, is described.
Visible Light-Mediated Synthesis of Enantiopure g-Cyclobutane Amino and 3-(Aminomethyl)-5-phenylpentanoic Acids
Kerres, Sabine,Plut, Eva,Malcherek, Simon,Rehbein, Julia,Reiser, Oliver
, p. 1400 - 1407 (2019/10/28)
A visible light-mediated [2+2] photocycloaddition of amide-linked dienes using [Ir(dtb-bpy)(dF(CF3)ppy)2]PF6 as triplet sensitizer was applied to generate a variety of N-tert-butyl, N-benzyl- and N-tert-butoxycarbonyl-protected 3-aza-bicyclo[3.2.0]heptan-2-ones in good yields and with good diastereoselectivity. Density functional theory calculations shed light on the conformational prerequisites for the [2+2] photocycloaddition. The bicyclic key structures could be readily transformed into g-cyclobutane amino acids. For the obtained racemic 3-phenyl-2-aminocyclobu-tane-1-carboxylic acid the resolution with chiral oxazolidin-2-one is demonstrated to allow access to both enantiomers. Alternatively, a chiral auxiliary approach led as well to the enantiomerically pure target compound. Finally, the synthesis of either enantiomer of 3-(aminomethyl)-5-phenylpentanoic acid, the racemate being described as an anticonvulsant is described.
Photochemical Synthesis of 3-Azabicyclo[3.2.0]heptanes: Advanced Building Blocks for Drug Discovery
Denisenko, Aleksandr V.,Druzhenko, Tetiana,Skalenko, Yevhen,Samoilenko, Maryna,Grygorenko, Oleksandr O.,Zozulya, Sergey,Mykhailiuk, Pavel K.
, p. 9627 - 9636 (2017/09/23)
We have developed a rapid two-step synthesis of substituted 3-azabicyclo[3.2.0]heptanes which are attractive building blocks for drug discovery. This new method utilizes very common chemicals, benzaldehyde, allylamine, and cinnamic acid, via intramolectul
Organozirconium-mediated solution- and solid-phase synthesis of 3-benzyl pyrrolidines and other potentially neuroactive amines
Hunter, Rupert A.,Macfarlane, Donald P. S.,Whitby, Richard J.
, p. 3314 - 3318 (2008/09/18)
An efficient route to 3-benzylpyrrolidines using a zirconium-mediated cyclisation both in solution and on a solid support is reported. 3-Benzylidine-pyrrolidines, 3-aryl-pyrrolidines and 4-arylpiperidines were also synthesised. Georg Thieme Verlag Stuttga
Radical cyclization in heterocycle synthesis. II. Total synthesis of (±)-anantine and (±)-isoanantine
Naito, Takeaki,Honda, Yuko,Bhavakul, Vanida,Yamaguchi, Sayaka,Fujiwara, Azusa,Miyata, Okiko,Ninomiya, Ichiya
, p. 1932 - 1939 (2007/10/03)
(+)-Anantine, (±)-isoanantine and related compounds were synthesized via two key reactions, sulfanyl radical addition-cyclization and stereoselective construction of the E-benzylidene moiety.
