@article{SchmidtHoelterKellingetal.2011, author = {Schmidt, Bernd and H{\"o}lter, Frank and Kelling, Alexandra and Schilde, Uwe}, title = {Pd-Catalyzed arylation reactions with phenol diazonium salts application in the synthesis of diarylheptanoids}, series = {The journal of organic chemistry}, volume = {76}, journal = {The journal of organic chemistry}, number = {9}, publisher = {American Chemical Society}, address = {Washington}, issn = {0022-3263}, doi = {10.1021/jo2002787}, pages = {3357 -- 3365}, year = {2011}, abstract = {The first total synthesis of the natural product (3S,7R)-5,6-dehydro-de-O-methyl centrolobine and various analogues is reported, using a highly regio- and diastereoselective Mizoroki-Heck reaction of phenol diazonium salts and enantiopure dihydropyrans. The assigned relative configuration was confirmed by single-crystal X-ray structure analysis, but a revision of the absolute configuration is proposed based on polarimetric measurement.}, language = {en} } @article{SchmidtStaude2011, author = {Schmidt, Bernd and Staude, Lucia}, title = {Desymmetrization of (R,R)-Hexa-1,5-diene-3,4-diol via Monofunctionallization and Rhodium-Catalyzed Allylic Substitution}, series = {The journal of organic chemistry}, volume = {76}, journal = {The journal of organic chemistry}, number = {7}, publisher = {American Chemical Society}, address = {Washington}, issn = {0022-3263}, doi = {10.1021/jo2001337}, pages = {2220 -- 2226}, year = {2011}, abstract = {A sequence of selective monoprotection and Rh-catalyzed enantioconservative allylic subEtitution is established as a desymmetrization strategy for C-2-symmetric hexa-1,5-diene-3,4-diol. A benzyl protecting group and ethyl carbonate as a leaving group emerged as the most useful combination with respect to reproducibility, stereoselectivity, and yield: A remarkable deviation from the normally observed regiospecificity of Rh-catalyzed allylic alkylations was observed for unprotected carbonates. In this case, a linear, rather than a branched alkylation product was obtained exclusively.}, language = {en} } @article{HolecRybačekVaceketal.2019, author = {Holec, Jan and Ryb{\´a}ček, Jiř{\´i} and Vacek, Jaroslav and Karras, Manfred and Bedn{\´a}rov{\´a}, Lucie and Budesinsky, Milos and Slusna, Michaela and Holy, Petr and Schmidt, Bernd and Star{\´a}, Irena G. and Star{\´y}, Ivo}, title = {Chirality-Controlled Self-Assembly of Amphiphilic Dibenzo[6]helicenes into Langmuir-Blodgett Thin Films}, series = {Chemistry - a European journal}, volume = {25}, journal = {Chemistry - a European journal}, number = {49}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {0947-6539}, doi = {10.1002/chem.201901695}, pages = {11494 -- 11502}, year = {2019}, abstract = {Racemic and highly enantioenriched 3-methoxycarbonyl, 3-carboxy, and 3-hydroxymethyl derivatives of dibenzo[6]helicene were prepared. The Langmuir layers of these helicenes were formed at the air-water interface and transferred onto solid substrates to afford Langmuir-Blodgett films, which were then studied by ambient atomic force microscopy and (chir)optical spectroscopy. Significant differences were found in the behaviour of the Langmuir layers as well as in the morphology, UV/Vis, electronic circular dichroism (ECD), and fluorescence spectra of the Langmuir-Blodgett thin films depending on the molecular chirality and nature of the polar group. The experimental results were supported by molecular dynamics simulations.}, language = {en} }