Kerres, Sabine and Plut, Eva and Malcherek, Simon and Rehbein, Julia and Reiser, Oliver (2019) Visible Light-Mediated Synthesis of Enantiopure gamma-Cyclobutane Amino and 3-(Aminomethyl)-5-phenylpentanoic Acids. ADVANCED SYNTHESIS & CATALYSIS, 361 (6). pp. 1400-1407. ISSN 1615-4150, 1615-4169
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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 gamma-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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | STEREOSELECTIVE-SYNTHESIS; 2+2 PHOTOCYCLOADDITION; CYCLOADDITIONS; PEPTIDES; PHOTOCATALYSIS; BETA; GABA; PHOTOISOMERIZATION; CONFORMATION; STILBENE; amino acids; cycloaddition; energy transfer; green chemistry; photocatalysis |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 20 Apr 2020 09:00 |
| Last Modified: | 20 Apr 2020 09:00 |
| URI: | https://pred.uni-regensburg.de/id/eprint/27357 |
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