Köln, Germany
Köln, Germany

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Soldevilla A.,Greinstr. | Perez-Ruiz R.,Polytechnic University of Valencia | Miara Y.D.,Greinstr. | Griesbeck A.,Greinstr.
Chemical Communications | Year: 2010

The fluorescence of caged phthalimide-serine couples 2 and 4 is up/down modulated by decarboxylative photorelease with fluorescence decrease (2) vs. moderate fluorescence increase (4) serving as reporter function. © 2010 The Royal Society of Chemistry.

Griesbeck A.G.,Greinstr. | Nazarov N.,Greinstr. | Neudorfl J.M.,Greinstr. | Heffen M.,Greinstr.
Green Chemistry | Year: 2012

The intermolecular photodecarboxylation of arylacetic acids 3-5 in water by use of stoichiometric amounts of N-alkylated phthalimides 1a,b was investigated by NMR and online pH- and CO 2-release sensing. Decreasing the electron donor capability of the arylacetic acids by 4-fluoro and trifluoromethyl substitution alters the efficiency of the photodecarboxylation and selectivity of the secondary reaction. A remarkable switch in reaction channel (A to B) was observed for perfluoropropionic acid. © 2012 The Royal Society of Chemistry.

Griesbeck A.G.,Greinstr. | De Kiff A.,Greinstr. | Neudorfl J.M.,Greinstr. | Sillner S.,Greinstr.
Arkivoc | Year: 2015

The photoxygenation reactions of the natural monoterpene aldehyde safranal (1 ) and its reduction product safranol ( 4) were studied and the endoperoxide 5 from safranol was isolated and characterized by single crystal X-ray analysis. A dyade synthesis using DCC coupling of safranol with artesunic acid delivered the reactive substrate 7 for 1,3-diene photooxygenation. Singlet oxygen reaction of the substrate 7 enabled the synthesis of the trioxane-endoperoxide dyade 8. The diastereoisomeric 1,3-cyclohexadienes 10 were obtained from the proline-catalyzed Diels-Alder dimerization of the Michael aldehyde 9. From the singlet oxygen addition with the diastereoisomeric substrates 10, only the kinetically preferred cis-endoperoxide 11 was formed. © ARKAT-USA, Inc.

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