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Beilstein J. Org. Chem. 2017, 13, 2833–2841, doi:10.3762/bjoc.13.275
Graphical Abstract
Figure 1: Molecular structures of AL-12, AL-12B and AL-5.
Scheme 1: Retrosynthetic analysis of AL-12, AL-12B and AL-5 (in their neutral forms) and their derivatives.
Scheme 2: Optimization study using phenylacetate 2a.
Scheme 3: Photodecarboxylative additions to N-(bromoalkyl)phthalimides.
Figure 2: Crystal structures of photoaddition products 3a (left) and 3b (right).
Scheme 4: Formation of 5 by photodecarboxylative additions.
Scheme 5: Acid-catalyzed dehydration of 3a–q.
Figure 3: Crystal structure of (E)-7a. Side view and front view.
Scheme 6: Amination of dehydrated products 7a–q.
Figure 4: Crystal structure of (Z)-8a. Side view and front view.
Scheme 7: Mechanistic scenario for the photodecarboxylative addition.
Scheme 8: Possible scenarios for nucleophilic cyclization to 4.
Scheme 9: Possible E/Z isomerization for compounds 8a–y.
Beilstein J. Org. Chem. 2013, 9, 2015–2021, doi:10.3762/bjoc.9.237
Scheme 1: General [2 + 2]-cycloaddition of furanones with alkenes.
Figure 1: Rayonet chamber reactor (RMR-600; Southern New England) with quartz test tubes. A 10 AU-cent coin i...
Figure 2: Microcapillary reactor. (a) Setup with inserted μ-capillary unit. A 10 AU-cent coin is shown for co...
Figure 3: (a) UV-spectrum of 1 (in MeCN) vs emission spectrum of the UVC lamp. (b) Light-penetration profile ...
Scheme 2: [2 + 2]-Cycloadditions of furanone 1 with cyclopentene (2).
Scheme 3: [2 + 2]-Cycloadditions of furanone 1 with 2,3-dimethylbut-2-ene (4).
Beilstein J. Org. Chem. 2011, 7, 1055–1063, doi:10.3762/bjoc.7.121
Scheme 1: General photodecarboxylation involving phthalimides (the broken line indicates intra- as well as in...
Figure 1: Microreactor (dwell device, mikroglas chemtech) under a UV exposure panel (Luzchem) and connected t...
Figure 2: UV-spectrum of DMBP (in MeCN) versus emission spectrum of the UVA lamp. The vertical dotted line re...
Figure 3: Light-penetration profile for a 1.5 mM solution of DMBP at 350 nm. The vertical lines represent the...
Scheme 2: DMBP mediated α-photodecarboxylation of N-phthaloylglycine (1).
Scheme 3: Photodecarboxylation of potassium phthaloyl-γ-aminobutyrate (3).
Scheme 4: Photodecarboxylative cyclization of potassium phthalimidomethylsulfanylacetate (6).
Scheme 5: Photodecarboxylative benzylation of 2.
Scheme 6: Photodecarboxylative addition of 11 to 2.
Scheme 7: Photodecarboxylative addition of 11 to DMBP.
Scheme 8: Mechanistic scenario (the broken line indicates intra- and intermolecular reactions).